A sissy visits the Headmistress

1. Miss Stern delivers both punishment and pleasure

I knocked timidly on the heavy door and heard Miss Stern's voice from within, commanding me to enter. I slowly opened the door and walked into the presence of my Headmistress. She was in her mid-fifties and sat behind her massive oaken desk as I came in, studying a heavy file. I stood still just inside the door, waiting for her to take notice of me. She briefly looked up, saw me standing there, and told me to close the door and approach her.

I was shaking with expectation and trepidation. This was my first time with Miss Stern. I had met her online, following an intriguing link I had found on a femdom website: 'Are you a sissy lesbian looking for schoolgirl training?'. The link had taken me to a page with information about a femdom Mistress, that is Miss Stern, who was willing to take on training of feminized males looking for a strict mature Headmistress to keep them in line and teach them how to be good well-behaved lesbian sissies. My slight, boyish frame tingled deliciously just reading about the specialized sessions this Mistress offered.

I'm twenty-three-years old, my birthname is Theo and I've known for almost ten years that I desire to be feminized and sissified. I have also discovered within me a strong craving for submitting to a mature woman, but I have not yet met someone who would like to dominate me. I am shy, I don't go to special clubs or gatherings. I have chatted online with quite a few people, including s few mature women.

Then that site popped up. With a picture of Miss Stern. Headmistress Stern. I paid for an online video chat session with her and she was very open and responsive to my wishes and desires. She did not play around, she said. I needed to be committed to her and to be trained, otherwise she felt it would just be a waste of time to meet. So, we had one more on-line session where I had to present myself as my feminized persona, Rose. She carefully instructed me on walking, sitting and moving as a woman, and also gave some advice on make-up and dressing.

I was grateful when she following those two sessions accepted that she would meet me in person, as Rose, and initiate a training program aimed at transforming me into a lesbian sissy. We made an appointment two weeks after that last on-line session and I was not allowed to touch myself inappropriately during that time and I was commanded to dress as Rose as much as possible. Yes, it cost me. Miss Stern did certainly not come cheap. But I have a medium-sized inheritance, and I had decided that I wanted to explore my deep desire for becoming Rose. After all, it was also her inheritance!

I had been the longest two weeks in my life, but now I was finally here, having driven a few hundred miles, dressed as Rose and with rising anticipation and excitement as I neared the city where Miss Stern resided. I parked near the given address and found her house -- a nondescript well cared for town house. I rang the bell and knew I was being scrutinized closely. A camera was very evident above the door. Then Miss Stern's voice told me to enter and make my way to the first floor, first door on the right.

I followed the instructions and now I was here, I her intimidating presence, dressed as Rose.

I made my way across the soft carpet and stood before her, a twenty-three-year-old sissy dressed as a schoolgirl as instructed: White blouse and dark blue tie and jacket; grey, medium length pleated skirt, blue woolen stockings and sensible brogues.

I stared at the carpet, avoiding looking directly at the imposing Headmistress. She finished whatever she was doing, and I felt her eyes on my trembling body.

"So, Rose, what have you been up to?"

"Nothing...., I..." I was very nervous.

"Look at me, when I speak to you, girl! And you may address me as Mistress Stern or Ma'am!"

I managed to look at her face, where the dark eyes gleamed with anger.

"Y.. yes.., Mistress Stern."

"Did you follow the rules we agreed upon, Rose?"

I shook my head trying to avoid her piercing eyes. I couldn't get it out. It was much too embarrassing.

"Oh, come on, you silly sissy thing. It's better to have it all out, and off your chest! What rule have you violated, Rose?"

Her eyes bored into mine, and I felt a warm tingling in my young sissy body. Miss Stern was a tall woman, and she dressed conservatively. She was wearing a black silk blouse with fluffy sleeves and a long black skirt that hugged her generous hips tightly. Her short-cropped hair glistened darkly in the yellow lamplight, and her face seemed suddenly flushed.

"I like my girls to look at me when I question them. I find it makes the truth appear much faster. Now, please explain what you have done. Have you pleasured yourself? Have you fondled your sissy parts and felt illicit excitement coursing through your sissy body?"

"I.., no Ma'am.. I wasn't.. I wouldn't.. I was.. My bosom, Ma'am!"

"Ahh, so you have been touching your sissy bosom! Did you also perhaps tickle your little nipples to see if they could get stiff?"

I had to look away, then. Away from this formidable woman who questioned me intimately about my offence. I had indeed tried to manipulate my nipples, to see how stiff they could get, and the action had caused a seeping wetness from my sissy clit. I could feel moisture in my cotton panties, making them stick to my tingling sissy parts. But I couldn't tell Mistress Stern about it!

"Hmm, you won't look at me, and you won't answer my question! Well, in that case, there is only one action possible: You must be punished!"

I had never been punished before, never received any corporeal discipline.

"I'm going to deliver a spanking, Rose. A good sound spanking of a lovely feminine or feminized bottom is often very conducive to the truth. I prefer the miscreant to stand with spread legs and bend forward with outstretched arms, so her upper body is flat on my desk. That way, I have unhindered access to the bottom of the sissy girl, and she cannot use her hands to try and avoid the discipline. Now: Assume the position!"

"Yes, Mistress Stern."

I hurried to comply with her order, and was soon standing with spread legs, my sissy parts pressed close to the desk and my upper body lying flat on the desk's wooden surface.

"Hmm, since it is your first time, I believe it will be prudent to secure you firmly in that position. Hold still, now!"

My Headmistress proceeded to tie a length of rope around my wrists and secure it to a convenient handle on a drawer at the other side of the desk. She then quickly tied each of my ankles with additional rope and spread my legs to the utmost by tying to rope to the massive legs of the oaken desk. In a very short time, I was thus immobilized and made eminently available for a spanking.

I felt Mistress Stern caress my upper thighs and buttocks through the fabric of my skirt and shivered with fear and some darker anticipation of the discipline I was to receive.

"So, how does my naughty little sissy schoolgirl feel? All tied up and ready for her spanking? Hnh? Are you ready for me to spank your firm butt, until it's red and warm and tingly?"

I was totally petrified and unable to answer her insidious questions. Suddenly a heavy hand fell devastatingly on my right, skirt-covered buttock.

"Answer me, you naughty sissy! You must answer the questions a Mistress puts to you promptly and truthfully! Otherwise your punishment will be much more severe! Now, tell me, Rose: Are you ready for your spanking?"

"Y..yes, Mistress Stern."

"A girl about to be punished, Rose, must always ask to receive her punishment. I find it helps in creating the proper humble attitude. So, have you been a naughty sissy, Rose?"

"Yes, Ma'am, I've been a naughty sissy."

"And what have you done, that is so naughty?"

"I.. I've had my hands under the blanket, Mistress Stern."

"Oh -- and what dirty and depraved things did those hands then do, my lewd sissy trollop?"

"They.. I... I touched my breasts, Ma'am."

"Yes, your sissy breasts. You did not answer my question before as to how exactly you touched and fondled with them, but you might have changed your mind. So: How did you touch your sissy boobs?"

"I... Mistress, I rubbed my palms over my breasts.. and used my fingers to.. to pull my nipples..."

"Mmm, and do you like to have your nipples pulled so they become all stiff and tingling and hot. Eh? Do you, you disobedient sissy slut?"

She stood behind me, close. Oh, so close. And she bent down over my bound body, whispering these indecent suggestions into my ear. Her hot breath scorched me; her hot words seared my sensitive flesh. Shuddering, with slick wetness seeping from my sissy clit into my undies, I tried to reply. And couldn't. My mouth was dry, and my breath uneven. Mistress Stern gently stroked my upper body, and her hands even found their way beneath my bound body and then she was cupping, through my school blouse, my small sissy tits in her knowing hands and pressing and releasing and pressing again, and I ached with vague longings that melted my protests. It felt, to my undying shame, most wonderful. My Headmistress teased my almost flat bosom for a long time, whispering her debaucheries all the while, clouding my sanity with her flaunting eroticism.

"Yes, my sweet sissy slut like to have her small sissy titties fondled, doesn't she? She like to have her nipples pinched and pulled... like this.. so stiff they are, the darlings... Yes, Rose, you naughty little sissy, you like such treatment, so you lie in your bed and touch yourself, indecently touch yourself... And I cannot allow that... Such nasty, naughty lesbian sissies belong to me, you see. You are mine to punish and tease as I, and only I, see fit. And you like this. You like being tied up and being forcefully fondled me, don't you?"

I could only moan incoherently by then. So, Mistress Stern gave my bottom a few hard spanks to wake me up.

Smack! Smack! Smack!

"Ouch! Oh... please no... I.. No, I don't like this... your hands on my tits.. No... Oh, please, no... don't spank me, please, Ma'am..."

"No? But of course, I should punish you! You have seriously broken my rules and it is my simple duty to see that you are strictly disciplined for your bad behavior. And besides, it's very good for a naughty sissy like you to have her behind thoroughly spanked by a mature and experienced, woman!"

Again she lightly spanked my vulnerable, exposed arse and the increased heat thus created in my bottom-flesh caused, to my great embarrassment, more juice to leak from my clit, which according to her instructions were kept tied-up at all times, and the viscous sissy pre-cum moistened the cotton panties that were stretched taut across my smooth buttocks.

So, there I was, bound to Mistress' massive oaken desk with my clothes in disarray and my sissy body strumming from her indecent manipulations of my bosom and backside. In addition, every time this intimidating woman called me a naughty sissy or a slut or talked about punishing or spanking me, I felt a growing excitement, a sweet palpitation, and a yearning to give in, to let her domination engulf me and swallow me up totally. I should fear her and her discipline, but instead I found myself longing for her hand to strike my posterior. I was a truly submissive lesbian sissy slut!

"Rose, you have been a very bad and naughty little girl. Pulling on your nipples, indeed! You must therefore ask me nicely to spank you and receive your just punishment. Repeat after me: I have disobeyed the rules set by my Mistress Miss Stern by having my hands under the blanket and pulling and pinching on my stiff sissy nipples. "

"I.. I have disobeyed the rules of my Mistress Miss Stern, Ma'am, by having my hands under the blanket and pulling and pinching on my stiff... my stiff... sissy .... nipples. "

Mistress Stern continued her instructions.

"I therefore humbly ask to have my bare bottom spanked, so that I can in the future learn not to disregard the rules set by Miss Stern."

"I therefore humbly ask to have my bottom spanked, Ma'am, so that I can in the future learn not to disregard the rules set by Miss Stern."

"Your bare bottom spanked, you naughty sissy!"

"My ba.. bare bottom spanked, Mistress Stern!"

"Very well, Rose. Since you ask so nicely to have your bare bottom spanked, I'll comply with your wishes."

She knelt down behind my bound body and slowly drew my skirt up, baring my pantie-covered rear. I was smooth and hairless below my eyebrows as instructed. I heard her inhale deeply and soon sensed a musky odor in the air. Shame made my cheeks redden because I knew that smell. It was the smell of my own, overexcited sex that spiced the air of Mistress Stern's office! And without a flicker of doubt, she knew it.

My Headmistress stood up, carefully bundled my skirt round my waist and proceeded to roughly fondle my exposed bottom cheeks through the flimsy white cotton panties stretched so tightly over my sissy behind. Her fingers dug heavily into my flesh and then small slaps rained down.

"Just a warmup, dear. To make you ready and hot for the real thing. But, ohhh, you are hot already aren't you? You naughty sissy slut! All wet between your little thighs. That sweet sissy clit of yours has been drooling sissy honey ever since you came into my office, hasn't it?"

She knew, of course, that it was so. She had me totally under her insidious spell by now, and there was nothing I could do, but admit to my shame.

"Yes..., yes Ma'am... I'm a naughty sissy slut and my .. my clit... had been wet... ever since I came into your office... Please spank me, Mistress, for being such a wicked, depraved sissy!"

"Oh, yes, you disobedient scamp! Spanked and punished your delectable bottom will be indeed! But first I want to bare those voluptuous orbs somewhat more. There -- that's much better!"

Miss Stern carefully collected the cotton material of my panties and bundled the moist fabric into a cord that bisected my bottom cheeks. She manipulated the filament, so it rubbed gently over my slick, wet clit. She upheld a persisting see-sawing motion with the bundled panties for a while, sliding the fabric over my sex and down into the cleavage between my buttocks.

"Now, my misbehaving trollop, I will start your spanking. But you must ask for each and every slap on your bottom. And also count each spank and give thanks to me, your Mistress, for imparting just punishment for your transgression and self-satisfaction. Do you understand, you miserable sissy hussy!?"

Unclean thoughts flowed through my muddled mind. It was extremely humiliating to be tied to Miss Sterns desk with spread legs and my blouse open. My nipples were achingly stiff from the ministrations she had subjected me to earlier, my skirt was raised above my waist, and as my Mistress tugged on my cotton panties my bottom lifted up slightly, with naked orbs begging for strict attention. I felt a longing, a sinful, perverted pulsation in my bared flesh and involuntarily clenched my buttocks.

I knew that I needed discipline and correction for my errant ways. Miss Stern was favoring me by chastising my young sissy body. I wanted her strong hands to whack my ass and fuel the fires stirring in my loins. The mere thought of this, the image of this majestic female disciplinarian, who was about to spank my vulnerable sissified schoolgirl behind, the exquisite debasement of my position: All this caused a strumming tightening in my sissy sexual parts and a copious flow of secretions. Somewhere, I found a voice, a little high-pitched sissy voice, submissive and deferent.

"Please, Mistress Stern, please spank my bare bottom...!"

Smack! Relentlessly the Headmistress let her hand thump heavily on my right orb. The barehanded smack stung tremendously, as she was using much more force than during the previous warming I had been subjected to. At the same time, she maintained her strong tugging grip on the bundled panties cutting into my tied-up sex. I almost forgot myself, but then remembered her orders.

"One. Th.. thank you, Mistress.... May I have another?"

"Yes, indeed, wench."

Smack! My other cheek was subjected to a whack of equal force, and the sting spread to encompass both my quivering hemispheres.

"Two... please may I have another, Mistress?"

"You forgot to properly thank your Mistress, you worthless sissy bitch!"

Slap! Slap! Two rapid and painful attacks made my posterior heat up.

"Now, again. Count from two!"

Smack!

"Two.., thank you for correcting me, Mistress. May I please have another?"

"That's much better, you naughty slut!. Yes, you may."

It went on for some time, this tortuous abuse of my gradually reddening behind. Miss Stern was an extremely competent flagellant and her spanking caused a warming of my flesh, which stung, but also caused an increased blood-flow to the tormented area. This heated up my buttocks and sparked a deeper, throbbing sensation, which fed my depraved pleasure at being in this immodest situation. Being forced to ask my Headmistress for each, individual slap caused me to focus and dwell on the predicament I was in, and perversely, this encouraged further lascivious feeling to erupt in my mind.

"Twenty, Mistress," I finally sobbed. "Thank you and may I please...."

"Well done, my sissy trollop! You may have another, but not just yet! I want you to relax for just a moment and savor the sensations my spanking has induced in your derriere. You have a most delicious ass -- it's been a pleasure punishing you!"

I blushed at the praise and felt suddenly very proud that I had stood up so well to my discipline session. So far. For it seemed Miss Stern had further plans. She did not free me from my undignified position, nor did she change the revealing position of my clothing. My panties, now soggy with my excretions, were still tightly pulled up between my spread legs, and my skirt and blouse were in disarray.

My spanked rear felt like it could glow in the dark. The thrashing had been severe and without mercy and the Headmistress had a firm touch when punishing an errant sissy. Fiery sparks of pain had been ignited and brought tears to my eyes, but the treatment my Mistress had given me, had also caused a numbness in my buttocks. The smarting pain now gradually gave way to a dull throbbing ache and a spreading heat, nourishing my already aroused deep desire to submit and be controlled.

Miss Stern now gently massaged my heated bottom cheeks. Her competent hands softly, but firmly, delved into the flesh she so recently had spanked.

"You've acquired a most delightful rosy red hue on your behind, my sweet sissy! Most becoming on a girl or a sissy, the color that suffuses into her skin after a proper delivered spanking. And the heat.... you do feel the heat, don't you?"

"Yes.. yes.. Ma'am I do feel the heat..."

"Good, and what does the heat of a well delivered punishment do to such a misbehaving vixen as yourself? Does it make you all hot and sticky between the thighs? Hmm, your panties are certainly very sticky with sissy juice! So, Rose, why is your little sissy clit wet, and why is my whole office smelling of your musk? Is it because you perhaps like to be in such a debased position and have your bared bottom touched by me? Hmmm?"

"It.. I.. please Mistress Stern... Yesss.. I like having my bottom... spanked... and your hands ... now.. touching me... there..."

"Where am I touching you now, you slutty sissy tramp? "

"On.. in... my.. sissy pussy... ohhhh... Ma'am.. please don't.. not there.. not inside.. Ohhh.. Miss Stern.. your finger... it's up inside me......."

"Yes, indeed it is! Right up inside your tight sissy pussy, my little girl. Lubricated with your own secretions, my finger is penetrating you now. Right up to the knuckle. Then out again... in.. out.. in.. out...."