Turned Into Full-Time Sissy Maid: Locktober Feminization Story, Part 2

Hello, darlings. Recently, we received a very peculiar email from one of our most loyal students. She said she wouldn’t need to join Locktober this year because her Mistress had been keeping her in chastity full-time for a year now, and she no longer felt even the slightest urge to masturbate like a man. We chatted for a while, and I found her story quite fascinating. I asked her to describe a day or a week of her life as a full-time sissy maid to maybe apply her experience to our free Training. Luckily, she’s a very articulate girl, and what I received in return exceeded all of my expectations. With her permission, I decided to share her reply with my students. I think it will be quite an inspiration to you. Take notes, girls.

This is Part 2 of her reply. Read Part 1 here.

“Lost in lued thoughts, I finished vacuuming and headed to a power socket at the opposite end of the hallway. I guess I was a bit clumsy in that turn and as I approached the socket I wobbled in my heels.

‘Emily!’ I heard through Ariana Grande’s beautiful harmonies in my headphones.

I turned around and noticed Mistress watching me with noticeable dismay in her look. Damn it, she saw.

‘Was that a wobble?’

‘No, Mistress… I mean yes, Mistress, yes, I wobbled a bit there,’ I murmured as I curtsied.

‘Unbelievable. Should I handcuff you to the treadmill again? Haven’t done it for a while actually… What was it last time, a record I believe?’

Oh, yes, the treadmill training. From time to time, when Mistress noticed me walking in a manner that wasn’t graceful enough, or god forbid when she caught me taking the heels off during the day, she would lock me into 5-inch stilettos with padlocks, handcuff me to the treadmill in our basement gym and leave me there for a couple of hours. This training was particularly frequent at the start of my complete sissification, and it had been two months since I last put on those heels. Now that I think of it, actually, it was me who once brought it up that I could practice walking in heels on a treadmill. As per usual, Mistresses took the idea and cranked it up a bit.

‘Last time it was 4 hours and 36 minutes, Mistress.’

‘Would be hard to beat these numbers, wouldn’t it?’

‘Please don’t, Mistress… I will be more graceful next time.’

‘You should be more graceful already.’ She paused for a second. Then her eyebrow arches softened and her look gained a caring feel. ‘But alright, I guess I can forgive my girl on her special day. Besides, until now you’ve been doing exemplary well. Can’t be mad for too long when my Emily looks so sexy,’ She passed by me and gently slapped my ass.

‘Wrap it up, sweetie, you’re going to be late for your pedicure.’

Indeed, it was almost 3 pm. Relieved and with a loving smile across my face I took away the vacuum cleaner and headed to my room to get ready for the appointment. Having something that required going out in the middle of the day with no prior notice was always stressful for me. Mostly, because of makeup. I had to make sure I washed it off completely, not leaving any traces, which was particularly challenging if I had been overly creative in the morning. And though my makeup was nothing special that day I still blotted my lips against tissues a couple of times to make sure there was no lipstick left. I also carefully probed my reflection in the mirror for traces of eyeliner or mascara. Girls might know that you can always tell if someone was wearing eyeliner or mascara when they have just wiped them off but it not being too noticeable was the best I could hope for.

Another source of stress was the perfume. At home, I always had to smell nice and feminine and so going out suddenly meant that I would inevitably carry that fragrance with me. If I knew Mistress had rescheduled my pedi, I would apply my perfume scarcely in the morning but that day in my overwhelming desire to make Mistress happy I had been rather generous.

And finally, there were clothing choices. With no clothes from a men’s section left in my closet, I had to be immensely creative to compose outfits that would pass as unisex. That day I went with a relatively safe choice. White high collar top, black urban slacks (with the most feminine thing about them being a waistline that was a tad high), small metal black chain and white Nike Airforces. Then I topped it off with a puffed khaki cropped jacket. Mistress said cropped jackets were the new trend among men as well but I didn’t think most of the passers-by on the streets were so well-versed in the world of fashion. Still, it was better than a rather feminine beige trench coat she bought me with its bodice clearly fitted for a woman’s waist. I took off my earrings, tied my dyed blonde hair into a low ponytail, grabbed the car keys and went to Helen’s beauty salon.

Helen was a friend of Mistress’s and I guess she knew a little bit about Emily. Mistress must have told enough for her to be very tactful and not to ask weird embarrassing questions to a guy who comes once in 3 weeks for a pedicure with gel colour and a simple no-colour manicure. She owned (and still owns) her neat little beauty salon and obviously, she had staff working for her but she always tended to me personally. I liked Helen, she was nice. Her overly positive attitude was always easing me up and I enjoyed chatting with her as she tended to my nails.

As I approached the salon I received a message from Mistress: “Do whatever Helen says. Do not object. I will be VERY disappointed if you do.” As you can imagine, that text scared the shit out of me. I had read too much feminization fiction to know that something rather dramatic awaited me in that salon. My first instinct was to run away but a month with no release does wonders for your pliability. So I just stood there in front of the salon’s doors, staring at my phone, too frightened to walk in, too horny to walk away, until the door opened and I heard Helen’s high energetic voice.

‘James, darling, hi, how are you? So nice to see you again! I’ve been watching you stand there for a whole minute. What happened? Did someone die? Jeez, I hope not, that was supposed to be a joke! Cool jacket, by the way!’

I liked Helen.

‘No, it’s alright. Hi, Helen. Coming in.’

‘Alright sweetie,’ she said as I settled down in one of the massage spa chairs. She called me “sweetie” as well but I guess I didn’t mind it,’ a little bird told me you have gathered up the courage for more experiments this time. Let me check… Pedicure, colour, gel, alright that’s usual… Manicure, colour, gel, extensions, design – ok, that’s new! Oh, and a cherry on top, eyebrows and lashes! So cool! I’m so proud of you sweetie!’

A WHAT? Oh, Mistress, why… How am I gonna…. God damn it.

Well, I didn’t have much of a choice, did I? Yes, indeed I almost didn’t have doubts that Mistress would let me out of the cage in the evening, but who knew what “disappointed” meant. Maybe she would force me into a ruined orgasm after a month in chastity, maybe she would be too harsh on my clitty, maybe… Ah, there were so many options and I wanted the safest one. Besides, “almost” didn’t mean “no” doubts. And I just wanted to cum. So, so badly. At the same time, why the lashes and eyebrows? Why today? The suspense was getting me even more excited, BUT THAT FUCKING CAGE…

Erm, I apologise for such foul language, Head Mistress, it’s just that my frustration with being locked was quite immense that day, and therefore I allow myself to swear occasionally in this email. I hope that’s OK. Right now, as I mentioned in my first email to you, I’m pretty used to staying in chastity all the time. But back then, on October 31st 2022, after a very harsh Locktober month with zero orgasms, ruined or not, my brain was spiralling with aggravation and anticipation of 00:01 emerging on the clock.

Anyway, red-faced and uneasy I replied,

‘Yes, that’s right. Elizabeth suggested I try something new and, well…’ Elizabeth suggested… Couldn’t I say something else that wouldn’t scream “what a sissy”?

‘Don’t worry, sweetie, I think you are very brave. You’ll look stunning when we are done with you!’ Helen said in her usual comforting voice as another two girls approached us. ‘Meet Kim and Elira, they will be helping me out today.’

‘Hi! James, right?’

At that moment a terrifying thought came across my mind. Sitting in that chair, greeting these girls, I wished I was Emily. Emily who could pass as a woman. The girls were trying to act as if nothing was out of the ordinary but that weird “James” gave out Kim’s excessive excitement. The one you hear in your sister’s voice when she suggests playing dress up as kids. However, if I was Emily then at least all these feminine beauty treatments wouldn’t be as humiliating. But if this lifestyle would continue and expand, and knowing my Mistress it would, that meant…

‘Elira will do your lashes and brows when we are finished with nails,’ Helen pulled me back out of my identity contemplations black hole.

‘Hi Kim, Hi Elira,’ I gently shook their hands trying not to look into their eyes.

‘Alright, to work!’ Helen said as she rolled her workstation next to my right hand and Kim settled down to do my pedi.

Soon the manicure and pedicure were done with, the nails were filed, the cuticles were pushed back and trimmed, the base coat was applied and it was time to decide on the design.

‘Beth mentioned you thought of French tips the other day,’ Helen said. ‘Nice choice! So, should we go with French?’

Of course, what else would Mistress select? The feminine classic. Hmm, would it be possible to stay at home for 3-4 weeks?.. I replied, 

‘Ah… Yes, I thought it would look quite pretty. Also, it’s pink for the most part at least, so it makes it a bit less noticeable, I guess…’

‘Well, don’t know about that but I see what you mean! Alright, French it is! Kim will manage with natural length but as for hands, I will need to do the acrylics, your nails aren’t long enough but don’t worry, nothing too dramatic, French is for classy ladies… or men, of course, sorry, haha!’

About one hour later I was a proud owner of French tip mani and pedi. The girls did an amazing job. It looked very pretty and very neat and… as feminine as a mani and pedi could be. Like Helen promised the acrylics weren’t too long but they were long enough for it to be quite noticeable. At that moment I realised that for some reason French tips looked even more feminine than a simple red manicure would. I was terrified by the result. But at the same time, I kind of admired it. And this feeling terrified me even more.

Next, I was handed to Elira. Straightaway she told me to just relax and trust her. If only she knew how many times I had heard that phrase at home – and usually it meant that “relaxation” would be quite hard to achieve. Well, after French tips, how much worse could it get?

First, she tended to my eyelashes. What a mysterious craft that is. Whatever it was that she was doing with tweezers while my eyes were closed didn’t instil any sort of calmness. Then it was eyebrows. Measuring, waxing, trimming, colouring, laminating (I think). Once she stepped back and looked at me, first intensely concentrated then pleased, she nodded and said,

‘God, you’re gorgeous. I’m done. Girls, have a look! Your natural eyelashes are a dream, by the way.’

‘Oh my God, James you’re so pretty! You’ll love this, come,’ Helen said as she led to a mirror.

Of course, I was expecting my reflection to be even more feminine now but what I saw was… a lot. I plucked my eyebrows regularly but these ones… They weren’t high feminine arches or anything that dramatic, they were rather basic, I guess, but they were just too perfect. Perfect shape, perfect colour, perfectly straight at the centre. There’s no way you could see these eyebrows and think ‘Well, he just looks after himself’. No, such eyebrows usually provoke something along the lines of, ‘Giiirl, you gotta give contacts of your eyebrows master’. As for eyelashes, well, what can I say, they were huge. Elira mentioned that she went with Classic so she didn’t add as much volume as she could have but it certainly didn’t look that way. Again, they were too perfect. Perfectly curled and perfectly long. Together with eyebrows, they somehow totally changed the proportions of my face, it was as if I had minor plastic surgery. Oh, Mistress, how far are you going to push me…

‘I’m… err… lost for words, to be honest,’ I muttered trying not to sound too terrified or too humble. It was hard to stay in James mode after seeing my reflection. 

‘I know, right?’ Helen said grabbing me by the upper arm and leaning her cheek to my shoulder as she was looking at my reflection with pride and excitement. ‘Damn, Beth, I’m jealous!’

‘Haha, same!’ Kim and Elira laughed.

Girls, you have no idea…

I paid for the services, tipped the girls for being so supportive and as I was leaving the place I swiftly glanced at my reflection in a full-length wall mirror next to the counter. With my crop puff jacket, and my stride, drastically altered after practically living in high heels for a full year, in the corner of my eye I saw a woman. I was used to this feeling and usually, I knew that if I looked more closely I certainly didn’t pass as a woman, not even close. The devil’s in the details after all. But now there were three more visible and super feminine ones. Well, at least I didn’t have to fear for Mistress’s “disappointment”.

After spending an unsafely amount of time staring at my nails while driving, I arrived home around 6 p.m. As I closed the front door, Mistress came down the stairs wearing a black satin mid-thigh robe, beautiful black lingerie underneath, half-finished makeup and her hair pushed back with a makeup hair band.

‘Emily! How did it go?’

‘Mistress, why did…’

‘Let me see, let me see!’

She approached me, investigated my face then took my hands and examined the nails. She brought her beautiful hazel eyes up, looked into my eyes and then suddenly kissed me on the lips. My poor clitty…

‘Good girl, Emily. I’m very, very pleased.’

‘Thank you, Mistress,’ I curtsied by instinct. 

‘You look absolutely stunning. Better than I even imagined. Helen and her girls are simply magicians. Let me write to her.’

‘Mistress, why did you…’ I interrupted her as she was turning away.

‘I think it’s time Emily has nails fitting her feminine divine,’ she replied without hesitation. ‘Besides, it’s now pretty normal for men. Eugine does his nails, have you noticed in work calls?’

‘Yes, but his…’

‘As for lashes and brows, I need your pretty eyes popping for today. And I think today you’d want me to have what I need, don’t you?’ 

‘Yes, Mistress.’

‘Good girl. Now, the girls took time with you so we are running late. No time for you to cook so I ordered some food. Have a bite and then meet me in my room, bathroom attire.’ Means my 5-inch slide-in marabou platforms, pegnoir, no lingerie. Okay, so most probably she has my outfit picked and will do my make-up and hair herself. But what for?

‘Please, hurry up.’

‘Yes, Mistress,’ I curtsied again and she ran back up the stairs. 

After such a stressful salon trip I would have preferred something more substantial than Caesar salad and grapefruit juice but corsets aren’t going to tighten themselves. 15 minutes later I entered her room wearing only pink heels and pink pegnoir. She was applying lip liner.

‘Wait a bit, please. Actually, come, watch, I saw this trick on TikTok yesterday, makes the colour deeper.’

As I stood beside her watching her finish her lips I couldn’t help but admire how sexy she looked. Again, most certainly deliberately to tease me. Her breasts rested in a black underwire Victoria’s Secret balconette bra, her legs encased in black stockings crossed and her right foot crowned with red painted nails hanging daintily straight, her incredible black hair cascading down her back, with the robe’s belt accentuating her waist…

‘Getting excited already?’ she interrupted my horny thoughts. With a closed lip gloss tube in her hand, she reached out to tap on my exposed clitty cage.

‘Oh, ouch, hehe… Erm.. Yes, Mistress, very much.’

‘I can imagine,’ she opened the lip gloss and started applying it. ‘Gotta wait a bit more, sweetie. Right now though I need you to calm yourself. Firstly, you need to get used to us girls wearing lingerie when getting ready. How are you gonna live through my friends’ bachelorette parties? Haha.’ I gulped. Seemed like she was joking… How little did I know back then.

She rubbed her lips together as she put away the lip gloss and continued, 

‘And secondly, we still need to clean your front. And we need to clean your bottom. Speaking of which, go grab your enema and clean yourself while I finish my hair.’

I did as I was told. I could very well be a nurse by then, the way I handled enemas. Right after I finished my 3rd flush, Mistress entered the bathroom, her hair neatly flowing down on one side, secured by invisible black pins on the other. 

‘You look beautiful, Mistress.’

‘Thank you, hun. Hands.’

I turned around and she handcuffed me behind my back. Then I sat down in the bathtub, hands under my butt, legs spread wide, eyes at the ceiling, trying to think of something horrible to avoid erection. Cold water Mistress used for cleaning certainly helped with that as well.

As she unlocked the cage she paused for a bit.

‘Wow, it does get smaller.’

I looked down instantly. My god, indeed. I’m a grower, so to speak, and my average 5.3 inches looked pretty small when flaccid to begin with. But now it seemed as if the length was reduced to the size of only my penis head. Clitty, no less. Or rather no more. 

‘Hey, what did I tell you, no looking,’ Mistress said as she slapped my inner thigh. I went back to staring at the ceiling.

‘Yes, Mistress. Sorry, Mistress. It’s just… It’s so small…’

‘I think it’s not permanent. But even if it is, you don’t use it as intended anyway,’ she replied as she finished cleaning the cage with antibacterial tissues.

‘Yeah, I’ve read it’s not permanent. I think I will research that again. Ouch,’ she pinched my skin a bit when locking the inverted cage back.

‘Sorry, hun. OK, that’s done. Take a shower,’ she instructed while washing her hands. ‘Use a scrub, please. Essence, lotion, the usual. Also, before that, hair mask. Did you add shower gel to enema? Why not? You know I like it better when it smells lavender. Anyway, you can flush yourself one more time while you wait with the hair mask.’

‘Oh, by the way,’ she stopped at the door, ‘your eyelashes, and eyebrows too actually, must not contact with water, so cleanse your face carefully. Also, they might get damaged by hot vapour so have a cold shower, please. Better for hair anyway.’

To be honest, cold shower did little to curb my hornyness. It was better than nothing, though. 30 minutes later I entered Mistress’s bedroom with my hair wrapped in a towel and another towel around my chest. My outfit for the night was lying on her bed. Pink lace thong, nude backless bra, chest lift-up stickers, breast forms, new small waist cincher, 4.5 inch see-through clear sandals in silver with wide toe strap, and… 

‘What do you think?’ Mistress asked lifting the dress up. 

That was… an interesting choice. A backless, tie halter neck mini dress in pastel pink, with cleavage and a flirty one-side drape coming from the accentuated waist down to the floor. It was nothing special, in fact, compared to even some of my maid dresses, it was quite simple but still, incredibly hot. A dress that would make a gym dude in the club approach you with semen popping out of his eyes.

‘It’s pretty. I like it very much. Thank you, Mistress,’ I paused for a second to figure out how to review the dress. Quite possibly it was a test but I had to be respectful. ‘Halter neck is pretty sexy, we can definitely work with cleavage and the drape is fun. Rather straightforward, though, maybe not the most fashionable dress I’ve worn. But I think with some accessories, silver maybe, and these clear sandals, which are quite trendy – again, thank you, Mistress – I think I will look nice.’

‘Yeah, not a runway dress,’ I breathed out in relief as she said that. I was right! ‘But I needed something conventionally hot. I don’t like the drape,’ damn, not so right after all, ‘but to an untrained eye it could add a fashiony flavour.’

‘I liked your verdict,’ she continued. ‘For the most part. I think we can trim your 4-hour weekly fashion research to 3 hours.’

‘Thank you, Mistress. Yes, you are right, now that I look at it again the drape might seem excessive.’

‘Emily, you don’t need to suck up. I said I was pleased with your reply. Besides, we still gotta see how it looks on you, doll. I think it will have to be a little less than 26.5 inches at the waist, though’.

‘Oh, ok, Mistress, as you wish,’ I said looking at the waist cincher with a slight owe. ‘Hmm, Mistress, no stockings?’

‘Why, wanna feel them rub against your legs, you horny girl? But no stockings for you this time. You have pretty legs plus those butt and leg workouts are paying off. No reason for you to hide them. Especially, with that French pedi. But we still need to accentuate them. Sit down, please.’

I gracefully sat down on her vanity chair, posture high up, back curved, legs together, ankles crossed to the side, hands on my lap. Towel or dress, the deportment training got deeply rooted in my movements.

‘Here’s the bronze shimmer. Apply it to your legs generously,’ Mistress said as she handed me some kind of lotion.

There was something so feminine about applying the shimmer to my legs while sitting down. Lifting my smoothly lasered leg up in a ballet arch, gently rubbing the lotion from ankle to thigh, seeing it become glossy and shiny like magic… I wonder if it’s possible to cum just with sheer willpower.

‘Legs to die for, sugar,’ Mistress brought me back from my sissy dreams to my sissy reality. ‘Take off the towels and put the peignoir on, let’s not rub the shimmer off’.

As Mistress started doing my makeup I realised why it was her who had to do it. I was relatively skilled at makeup. After all, I’d been educating myself for around eight months by then, trying stuff out, watching YouTube tutorials and TikToks, testing different products. Besides, on Thursday evenings I was supposed to come up with something sophisticated and trendy for Mistress to review. However, I was nowhere near her level yet. And apparently, my makeup for the night was supposed to fit my new lashes and eyebrows – it had to be perfect.

Mistress opted for pink and silver smokey eyes with a sparking pallet, rosie cheekbones and a generous amount of highlighter, a pointy contoured nose and nude pink wet glossy lips. She made me wear coloured contacts as well, which made my pupils larger and added a bright grey colour to them. I also learned that you had to be very careful with mascara on eyelash extensions, as opposed to my usual limitless strokes, and that you should avoid putting makeup on eyebrows that had just been done (Mistress put just a little bit to contour the ends). A Barbie updo with curled side strands crowned the look and… Damn I still remember how gorgeous that makeup and hair were. Obviously, I have some pictures Mistress made but the way my eyes, visually enlarged by lash extensions and laminated eyebrows, popped and sparkled, the way my lips, plumped with a volumizing lip balm, caught the light and shined, the way my blonde side hair strands contoured my diamond shape face, the way this look made me feel so dainty, so feminine, so hot and so powerful for some reason – that I will never forget.

‘Wow, Emily, you pretty girl. Look at you, pouting your lips and posing, haha. What a little minx have I brought up,’ Mistress said admiring her masterful work in the mirror. 

‘Oh, Mistress, you’re making me blush!’ I replied theatrically. Don’t know what came over me… Well, actually, I know, but still, it was so unlike me.

‘Thank you, Mistress,’ I said more appropriately for the usual Emily. ‘I’m mesmerized… That was a sheer masterclass.’

‘Now you’re making me blush!’ Mistress laughed. She was really pleased with her work and her mood elevated even more – which was good news for me and my clitty. ‘One day I hope you’ll be doing my makeup just as flawlessly. Alright, time to dress up. Need help with cleavage?’

‘No, I think I’ll manage.’

‘OK. You’ll definitely need help with that cincher though.’

As I reached down to the panties Mistress interrupted me,

‘Oh wait, almost forgot. I have a little something for you,’ she opened one of her drawers and took out a new remote control anal plug which seemed a little bit bigger than the usual ones. I should’ve guessed. ‘Bend down.’

‘Mistress, I… I’m… It’s so hard for me right now as it is, are you sure that’s necessary? I mean, I suppose there’s still quite a lot of time…’

‘Bend down, please. I won’t ask a third time,’ Mistress said in a very cold tone while putting her black glove on.

‘Can we…,’ I stopped the thought as Mistress put her hand on her waist and stood in a pose of an irritated wait. ‘Yes, Mistress.’

Defeated and terrified of testing my hornyness limits I put my arms on the bed and placed my feet, still in marabou sandals, wide. Cold lube, two-finger probe, and then the all too familiar feeling of tension and release as the plug settled in my ass.

‘You may stand up.’

As I raised back the sensation of my ass being full, the oddly pleasant rubbing inside and my prostate clearly enjoying the pressure made me consider if the locks on my cage were firm enough to hold up my clitty bursting with life deep inside the cavity.

‘6 inches long, 3 inches wide, went in so smooth… I trained your pussy well, Emily,’ she said while taking the glove off. 

‘Thank you, Mistress.’

‘Unlike your manners, apparently. When I tell you to do something, you do it. If I need your input, I’ll ask for it. That’s the basic math of you getting an orgasm tonight. You’re not a dumb girl, Emily, I thought you’d figured it out by now. I would have spanked you if we had spare time.’

‘Yes, Mistress, I’m sorry, Mistress. I will do as I’m told.’

‘Good. Now get on with that cleavage.’”

End of Part 2. Part 3 coming soon…

Isn’t it a dream sissy life? Tell me about yours in the comments…