Sissy's First Day

Sissy let out a disheartened groan as he closed the classroom door. He looked down despondently at the discipline demerit clutched in his gloved hand, "It's my first day and already I screw something up; I can't believe this."

It was only his fourth hour here at the Academy, and already he recieved a demerit. He wasn't quite regretting his decision to enroll in the three month maid training course, but he did think it was a bit unfair that the instructors were so strict on the first day. "How do they expect me to know how to curtsey properly on my first day?" Sissy lamented as he made his way towards the Dean's office.

Sissy had always fantasized about French maids, subservience to women, and submission in general. The thrill of being all dolled up and uniformed while at the beck and call of a stern, controlling woman always weighed heavily on his mind. Though as shy as he was, Sissy never sought to sate his secret desires.

It wasn't until he stumbled upon an advertisement for Madame Monique's Maid Academy that he decided to act on what was within himself. He did a little research, and found that not only was it a legitimate business, but it was apparently highly acclaimed in the BDSM world. The tuition was rather steep, but it included room and board on the Academy grounds.

After much self encouragement and a comfortable, relaxed interview with the Headmistress, Sissy finally enrolled. From the discovery of the ad to moving into his dorm room, the whole process only took two weeks, and every single day felt like lightning fast rollercoaster ride for Sissy. After all, two weeks ago he was hiding a maid's Halloween costume in closet and now here he was, quivering in confusion and about to be punished for the first time.

The dark, Victorian hallway was such a foreboding sight for Sissy as he timidly made his way to the Dean's office. The clicking of his high heels echoed throughout the baroque trappings of the hallway. The rhythmic clicking not only served to remind Sissy of his aching feet (which have been encased in these ungainly, six-inch stilettos for almost half a day) but also began to play on his nerves.

"God, I wonder what I am in for." Sissy muttered while his mind raced with devious fates he either fantasized about or saw in a horror movie. Distracted with his fantasies, his toe caught the edge of the carpet. "Fff..." Sissy hissed between his clenched lips, trying desperately to keep from letting his curse echo down the chasm-like hallway as he tumbled onto the ground; a mess of black and white lace.

Frantically, Sissy craned his head up and looked down both ends of the hallway, hoping to God that none of the instructors noticed. "Whew!" he sighed as he unceremoniously helped himself to his high-heeled feet, "Judging by how strict they are here, I would have gotten another demerit for sure."

Sissy ran his gloved hands down the front of his Maid's uniform and smoothed out any wrinkles that were caused by the fall. He then reached up and smiled wryly as he adjusted the frilly little Maid's cap that rested atop his head. That little cap was the most emasculating piece of his ensemble, especially atop the tight fitting, black wig that the Headmistress had assigned him to wear. The Headmistress apparently assigned wigs to each maid-in-training on an individual level and she felt the bobbed sides and short, cropped bangs of this 20's style wig suited Sissy's pale skin.

Sissy was a bit surprised to find that, as he rose, he was standing directly in front of a door labeled, 'Mme. Charlotte, Dean of Discipline.' Sissy drew up a thin, timid breath, "Well, here goes nothing." And with that, he knocked on the door. For a couple tense moments there was nothing but silence. Sissy was about to breathe a sigh of relief when an unmistakably feminine voice came from beyond the office door.

"Come in."

Sissy twisted the brass handle and slowly swung the door open. Almost immediately he was greeted to the sight of an incredibly beautiful and shapely woman bent over a desk and rummaging through a stack of paperwork. Sissy's crimson lips parted involuntarily as he took in the sight before him, from head to toe. She stood on tall, tawny pumps, the kind that tensed the calf muscles just right. As Sissy's eager eyes wandered up, they involuntarily traced the line running up the back of this elegant woman's stockings as they disappeared behind the hem of her tan, knee length skirt. Further up, her long, golden hair spilled down her arched back.

With a divine fluidity, the woman turned around, still shuffling a stack of papers in her hands. Sissy, stunned by the Dean's intense beauty, was even more stunned to see that he was looking up at her, literally. She must have been well over six feet tall in her shoes, and she exuded a confidence that made her seem even more majestic.

"Why, aren't you the sweetest looking thing?" She said, while tilting her head to look over her reading glasses.

Sissy, pulled from his stupor, quickly curtseyed and greeted the Dean, "Hello Madame Charlotte, my name is Sissy; it is a pleasure to meet you."

She let out a slight giggle and smiled slyly at Sissy's greeting, "So very polite of you Sissy. Now, how can I help you dear?" She set down a stack of papers and crossed her arms over her ample chest, pushing her breasts up just a little higher through her partially buttoned blouse.

Sissy, now quite embarrassed, held out the demerit.

Charlotte recognized it immediately. "My my, not another naughty one."

Any urge to defend himself seemed to steadily be draining away in the presence of this Amazonian, yet utterly feminine woman; all he could do was lower his head.

Charlotte made two steps towards Sissy and rested her lithe hand on the quivering maid's shoulder. "Don't worry little one, I'll go easy on you. It is your first day after all." She then cocked her head to the side and smiled as a golden curl slid from the frame of her glasses and over her cheek, "I don't get nasty till the second demerit."

With that remark, she turned around and began walking towards a large padded bench in the corner of her office. She placed one hand on the bench and turned to face Sissy, still standing perfectly still after her dire warning about a second demerit. Charlotte held out her hand and gently beckoned for Sissy to approach.

Filled with apprehension, Sissy walked as best as he could manage on his wobbly heels.

Charlotte slipped behind the maid in training, placed her hands on his hips, and guided his waist to rest against the bench's padded frame. A leather strap was then wrapped around Sissy's corset-narrowed waist and buckled in place. "Don't worry your pretty little head off little one, some of the maids actually get a little of enjoyment out of this." Madame Charlotte whispered as she strapped the waist restraint in place. She then gently slid her hands up Sissy's back. Reaching his shoulders, she softly eased his body forward, until his uniformed torso was resting horizontal against the bench's padded top. Charlotte moved with fluidity and grace, as if she had been doing this for years. Sissy's dangling arms were then secured to wooden struts leading away from the bench, as well as his ankles.

Charlotte traced her fingertip along the crescent of pale exposed skin revealed by Sissy's short skirt and stockings, and delighted as he struggled in vain against his restraints. She reached for a riding crop hanging from a brass hook on the bench, "So when did you decide that you wanted to serve women as a French maid, Sissy?"

He swallowed hard as he struggled to come up with an intelligible response. "Just a couple weeks ago Madame Charlotte," he answered as he felt the back of his skirt lifted up, allowing a chill breeze to caress his pantied bottom.

"My, aren't you the impulsive one." She responded, sliding those frilly panties down to Sissy's knees. Charlotte smiled as she noticed Sissy's fully erect cock. She knew that he was one of those types who craved this kind if discipline, whether they consciously realized it or not.

Deciding not to call attention to Sissy's raging erection, Charlotte softly patted his naked, smooth bottom. "Just one more thing left." She stated as she reached for a small egg timer. Deftly, she wound the knob until the little arrow pointed to the sixty second mark. Setting the timer in front of Sissy's eyes, she pressed the start button and disappeared behind his helpless form.

The timer ticked down. 60... 59... 58... 57... Every click set Sissy's nerves on edge. He held his breath as he wondered why nothing was happening. And that's when the blows begin to fall.

Madame Charlotte's crop began to rise and fall over Sissy's pale ass with shocking speed, leaving bright pink, square shaped welts all over his cheeks. Every muscle in Sissy's body clenched at once as the inhuman pain spread through his lower half, struggling in some desperate bid to get away from the merciless Dean. 40... 39... 38... Sissy's eyes began to well up with tears at the agony he was enduring. He just couldn't believe it; three or four slaps were landing with every second that ticked by. He felt like a panicked animal, fearing for his life as Charlotte's skillful cropping tore into his sissy ass.

The stern Dean placed one hand on the small of the helpless maid's back, seemingly to soothe him as she furiously beat his bottom. 10... 9... 8... Watching Sissy's expression intently, Charlotte whispered, "Just let it all go little one, just let it go." and then begin to crop his reddened ass even harder, as if she was beating out the last vestiges of masculinity left inside of him.

It proved just enough incentive for Sissy to let it all out. He began to sob and cry uncontrollably as hastily applied mascara ran in rivulets down his cheeks.

Charlotte's face began to flush in response to Sissy's emotional display; she let out a satisfied, low moan. Inspired by his complete release, she began smacking harder and harder in pursuit to squeeze every drop of pain out of the uniformed submissive. For the last couple ticks of the timer, the crop whizzed high over the Dean's head only to fall again over every square inch of Sissy's welt covered ass; blows landed several times a second.

Sissy's girlish sobbing grew even louder as the last few strikes landed home, almost completely oblivious to the fact that the timer's little arrow just ticked past the one digit. A tinny buzzing erupted from the timer and suddenly the rapid smacks of a severe cropping no longer echoed in the dark office. Sissy laid there, completely motionless except for the tremors caused by his soft whimpering.

Just a bit winded, Charlotte hung her crop on the padded bench and looked down to see Sissy's cock still just as hard as ever. She grinned to herself, knowing that this one will definitely be signing up for another semester.

Compassionately, the Dean helped Sissy to his wobbly feet. She looked like some sort of angel through Sissy's teary eyes. She slid her hands down the front of Sissy's uniform and smoothed out the wrinkles in his apron, "Now, that wasn't so bad, was it little one?"

Still breathing heavily and struggling to maintain his composure, he could only nod his head.

"Well, I suppose that was all the motivation you needed to maintain your best behavior from now on." Madame Charlotte said as she blotted a tissue over Sissy's face, cleaning up the tears but doing little to remove the mascara stains. "You may head back to class Sissy, the instructor s probably expecting you." The Dean guided Sissy to the door by placing her hand on his bottom. "And just so you know, that timer goes up to thirty minutes, little one." She told Sissy as he stepped out the door, quite in awe and fear of this beautiful woman. And with that, she shut the door and Sissy was alone in the cavernous hallway once again.

Feeling quite humiliated, emasculated, and humbled all at once, Sissy sniffed and began the slow walk back to his class room. He didn't take more than two steps when his instructor turned the corner and began walking straight towards him, quite an imposing sight in her patent leather body suit, black boots, and long black hair.

"What has been taking so long you little bitch!" she howled at the cowering maid. The domineering instructor already looked liable to break every bone in Sissy's body, but her eyes widened in rage at the sight of the mascara stains running down his cheeks. "What is this? Can't you even apply makeup correctly?"

"But Madame, I was just... "Sissy stammered, but was immediately cut off.

"Don't you dare backtalk me bitch!" She hissed as her black nail polished hand raked across Sissy's face with a powerful slap. Sissy crumpled on the floor from the force of the blow.

Standing over the meek little maid, the instructor produced another discipline demerit. "Take this and return straight to the Dean, and for your sake you better wash before you return next time." She barked as she tossed the demerit in Sissy's lap and walked away.

Sissy braced himself against the wall and rose again to his high-heeled feet. He then gave himself another once over, as he had been trained to do, to fix any imperfections in his uniform. Smoothing out all of the wrinkles and straightening all of the seams, Sissy began the walk back to the Dean's office, all while thinking about that timer going up to thirty minutes.