This is a continuation of the Doing Things Properly story. It consists of very strict, rigorous Femdom D/s and sissy training and humiliation. If this isn’t your thing, then please move on. For those who appreciate this type of story, consider rating it favourably and commenting positively.

———————————————————————-

‘You’ll wear this one today. And every Sunday until I say otherwise.’ Mistress placed the garment on the bed next to me. A maid’s outfit, at least that was its cut and style. But it was much more than just a simple, plain, conservative-styled and functional maid’s outfit. As I was about to figure out.

‘But first, the undergarments to go with it.’ She opened the bottom draw of my plain grey dresser, the one labelled, SISSY MUST NEVER OPEN.

I stood at attention in the small basement space that passed for my room, head up, shoulders back, arms straight, fingers together and pointing downwards, legs and feet together, naked, bar for the small steel cage I wore over my sissy clitty.

I watched Mistress as she crouched down and removed several garments from the draw. All in the same material as the maid’s dress by the look of it. My throat was becoming dry – I had difficulty swallowing. I already knew from my first six days here that she was an exacting taskmaster, intent on drumming into me the art of service, servitude and total obedience.

I knew by now that these ‘clothes’ weren’t something that I could lose myself in while undertaking a task or learning something new. No, these were designed for something else, something quite uncomfortable.

She stood back up and placed the assorted items down on the bed. ‘Right. Let’s deal with your ridiculous excuse for a real man’s cock first.’ I blushed and with those words hovering, she drew a small key from the pocket of her dark grey pants and unlocked the small padlock securing the tight cage around my clitty.

She tossed the device and key onto the bed. It felt such a relief to be free again after the intense feelings of discomfort and pressure – and, I must admit, a certain sexual frustration (well, I was now living my ‘dream’ of serving a strong-willed Woman!).

Mistress pulled a pair of pink latex gloves and a small tube of Dencorub ‘Extra Strength’ from the pocket of her aran navy cardigan.

I guessed what that was gonna be used for, simply hoping it wouldn’t be as bad as the hot chilli treatment she used on my first day here after my pathetic attempts at shaving off my body hair. I tried to blank my mind. Mistress put the gloves on.

‘Do you know why I am doing this?’

I swallowed again. ‘To help teach me that my clitty serves no purpose other than to amuse you, Ma’am.’

‘Very good. Those 250 lines on Friday night seem to have worked their magic.’

How could I ever forget that lesson? It took me most of the night – and various strokes of her cane for my many mistakes – to complete the lines she had set me regarding the role of my clitty, henceforth.

It was sheer torment – Mistress there in the room to supervise me the whole time (she on her computer, doing work), each letter written in different coloured ink, every letter individually written out, in a precise order, with any mistakes immediately brought to her attention for swift punishment.

She squeezed the paste onto her gloved fingers and moved in front of me. I took a deep breath as her other hand grabbed the head of my clitty and stretched it out hard and tight.

She began rubbing the paste over the shaft and into my ‘sissy-ovees’ (that’s what I had to refer to them as now) and over the scrotum. I grimaced as I felt her push back the slit of the head and smear paste into it. Oh…not good….

She stood back up and removed the gloves then picked up an unusual item from amongst the assorted garments. She stepped next to me just as I felt my clitty and sissy-ovees and scrotum warming.

‘This little bag should help keep you even more centred on today’s lessons.’ With that I found my clitty and ovees enclosed in a thick hessian bag, filled with some horridly sharp, highly annoying substance.

‘Horse hairs. Straight from my dear friend Jennifer’s stables and to a clitty near you!’, she laughed as she tied off the bag. ‘I can not have your clitty loose and free without a reminder that it needs to behave itself now, can I sissy-philomena?’

It had taken her three days to decide what my name was to be. It didn’t matter that I hated it — Mistress said she liked its air and waft of being old fashioned, prim, and ‘correct’. And ridiculously, unavoidably ‘girlie’. But what girl has a name like Philomena these days?

After announcing my new ‘Forever Name’ in the morning, Mistress had me spend the best part of that day learning to use a sowing machine, including stitching my new name onto about one hundred small, cloth name tags. These were to be hand sown onto my garments.

‘Yes, Ma’am,’ I just managed to say as a wave of intense heat hit my nether regions, buckling my knees.

‘Excellent!’

Another hessian item was picked out — panties, complete with lace trim. Mistress bent down and tapped my calf – I lifted one foot, then the other, as she put them over my feet. She began to draw them up as another wave, another knee bend, hit.

‘It’s gonna get a lot worse sissy-philomena. Right now, you need to focus on holding yourself together while I dress you.’

I exhaled heavily. ‘Yes Ma’am’. I couldn’t help myself – I let out a little whimper.

‘Awww, there, there, it must be terrible in there,’ she said as she put one hand over the hessian bag and shook it, sending new waves of pain shooting out. I cried out in pain.

‘You have permission to cry and whimper. But I expect you to maintain your posture.’

‘Yes Ma’am, thank you…arrrhhh! Oh…thank you..arrrrhhhh!! Ma’am for your kindness in….aaaa…letting me cry and…oh…whimperrrr….’

She laughed again and finished pulling the high cut ‘panties’ over the hessian clitty sack.

A bra followed — in hessian of course, also lace trimmed. Mistress fitted two small balls of dense hessian inserts into the cups. I was almost in tears by the time a pair of thick ‘hose’, for want of a better term, were pulled up high over my panties and up to my belly. She looked me up and down.

‘Awww, poor sissy-philly. Girls need a good cry at times,’ she said in a mocking tone as she lifted the maid’s outfit off the bed.

‘Arms stretched out, bend over.’ Easier said than done, but I obeyed.

The dress went over my head and shoulders. ‘Stand back up.’ She pulled the garment down and fitted it over my body, buttoned up the back, drew in the sides, tied off the cloth apron at the back then arranged the lace collar properly. My legs and belly were already being assailed by an intense and uncomfortable itchiness — now my arms and chest were, too.

‘Nooo…my God…this is… unbearable!’ I screamed, as I started jigging about and scratching my body madly.

‘Now, now, sissy-philomena, I’ll not have you jumping around like you have ants in your pants,’ said Mistress. ‘Or I just might have to put some real ants in your pants.’

‘Please, please, Mistress…this is…arrrrr….’ – I doubled over once more — ‘…arrrr….I can not….arrr…please…make it…stop…’ I pleaded, the tears flowing freely by now.

‘You know I can not do that, sissy-philomena. You’d lose all respect for me if I suddenly softened just because you pleaded for relief. No, there’s a very good reason you’re dressed this way today. And do you know what that is, sissy-philomena?’

The scratching and crying continued as I responded shakily. ‘No-o-o-o, Ma’aa-am’.

‘So you learn to endure and to persevere, regardless of any obstacle or challenge placed in front of you. That’s most essential for a sissy to learn, is it not, sissy-philomena?’

I whimpered acknowledgement.

‘You already know you are not here for any other reason but to serve my needs. You have willingly chosen that course. And I am gonna help you learn to serve me with all your very being, in whatever way, shape or means I decide, 24/7, 365 days a year. Is that not what you asked for, sissy-philomena?’

Through the tears I managed to squeak out a ‘Yes, Ma’am’.

‘Then there’s nothing more to be said. You’ll endure the hessian uniform for the day while you learn how to properly scrub and polish the upstairs floors. And then, you can spend a couple of hours in quiet reflection back here, while you sow your name tags on your assorted garments.’

‘Yes, Ma’am’.

‘But first, we mustn’t forget your posture collar. Your last day with it on. For now, at least.’

The tears were flowing as Mistress placed the collar around my neck and buckled it up firmly.

‘That’s better. Much, much, better’, she said as she stepped back to take in my appearance. I was scratching myself and moving about again.

‘Sissy-philomena, STOP scratching NOW and stand at attention’. She pointed to the mirror. ‘In front.’ I obeyed instantly.

‘That’s better. You’ll stand like that for the next 30 minutes. You can whimper and cry as much as you like. But under no circumstances are you to scratch or jiggle about.

Is that clear?’

I absorbed her words, took a very deep breath and composed myself before quietly answering. ‘Yes Ma’am, perfectly clear. Thank you for giving me this opportunity to learn another lesson so I can be the best feasible sissy for you.’

‘We’ll see about that.’ With that she turned around and walked away, back up the stairs.

Oh, how I wanted to wipe away my tears…and scratch my entire body…and take the horse-hair pouch off…but of course I did nothing of the sort.

I closed my eyes and began to control my breathing, began to centre my thoughts so I could quiet them down and then set them apart…focus, sissy, focus…you must do things properly…