Turned Into Full-Time Sissy Maid: Locktober Feminization Story, Part 1

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.

“Dear Head Mistress Alyssa,

Yes, mam, it does feel like I’m living every sissy girl’s dream. There are days when I will wake up and pinch myself just to make sure it’s all real. Fortunately, it is. I’m such a lucky girl! Not to say that it’s easy, though. It’s rather challenging and tiring at times. It was especially hard at the start of my journey. My Mistress, who I’ve been married to for one and a half years now, is very strict and demanding, and it took me a lot of time and work to live up to her standards. Or at least to get closer to them, I think… Many things were happening against my will, but in the end, sissification is supposed to be forced, I guess. Still, I’m thankful to my Mistress beyond words, and even after the most tiring days in 5-inch heels, even after the harshest punishments and challenges she bestows on me, I feel happy and content. I reckon some people are just born to be sissy maids. And some people are definitely born to be feminization Mistresses.

Thank you so much, mam, for your interest in my daily life. I’ve thought about your request for a while, and there’s one particular day that would describe my experience most completely. Besides, it’s related to Locktober. I’m going to talk about October 31st, 2022. I will change all the names, except mine. Also, I’m not a native speaker, so I apologise for potential mistakes.

That day, I woke up in my own small, girly bedroom at 5:30 AM, as usual. By then, I’d gotten used to the not-so-pleasant morning sensation of my clitty trying to get hard in my inverted chastity cage; however, that day, it got really intense. I was very excited. Our second Locktober with Sissylover had come to an end, and it was a harsh one. I thought it would be easier this time with all my experience in chastity, but not only were the tasks tough, but my Mistress introduced an additional challenge: I wasn’t even allowed a ruined orgasm with a vibrator. There was something so humiliating about the fact that not only the keys to my cage were in my Mistress’s hands, but all the vibrators were hidden from me as well. But I guess you can’t argue with the results: at times when my cravings for a release were especially potent, I would catch myself dreaming about rubbing a magic wand against my cage instead of jerking off as a normal man would. That morning, I felt the same urge. My whole body was aching for a release—and, hopefully, I was going to get one today.

I stood up, slipped into my 5-inch pink marabou slide platforms that Mistress made me wear instead of home slippers, and headed to the bathroom. Peeing while sitting down like a girl was something that I had been doing for a long time, even before Locktober, so it wasn’t something out of the ordinary. When I was brushing my teeth, I noticed several very thin and very scarce patches of morning shadow on my chin. That amount of hair would be more appropriate for a 15-year-old boy and not a 28-year-old man, but the electrolysis Mistress had signed me up for five months ago was bearing fruit pretty evidently. Applying body lotion after taking a shower also reminded me how thankful I was to Mistress for making full-body laser hair removal a regular thing for me. Before that, for a couple of months, I started every morning by shaving off any trace of hair I might have had on my body, which was making me wake up even earlier. Now all I had to worry about was the nurse chuckling at my chastity cage every 4 weeks or so (yes, Mistress always makes sure I’m wearing a chastity cage for laser sessions).

Once I shaved off whatever facial hair I had left and did my morning skincare routine, I pranced back into my room to do my work makeup. Mistress and I have a small business, and I work from home for about 3 hours in the morning every day (that’s why I have to wake up so early). So wearing make-up for work is not that big of a deal. After all, I am “the doll face and the plump butt of our company,” as Mistress says. By the way, that means I must wear appropriate clothing as well: a pencil skirt, a blouse, a blazer, hosiery, stiletto heels, accessories. Mistress considers my work dress code to be one of the greatest sissification ideas she’s ever had, and it’s hard to argue with that. The benefits of remote work! However, it wasn’t fun for me when the next day after Mistress imposed this rule on me, I was trying to hide my bra under a semi-transparent blouse during a Zoom call with our employees. Thankfully, if I had a work call, Mistress allowed me to wear very simple, barely noticeable makeup. She also let me style my shoulder-length dyed blonde hair in a unisex way, which was a challenge in itself, to be honest.

I didn’t have any work meetings on October 31st, 2022, so, according to Mistress’s instructions, I did full makeup, which I crowned with elaborate eyeliner arrows and bright red lipstick. “Hm, I think I will do chocolate smokey eyes with pink pastel lips for the evening; it goes well with that black gown,”, I thought as I reviewed my makeup look in the vanity mirror. I couldn’t stop thinking about the evening. When I was pulling up my nude stockings, my caged clitty started getting excited again. “Fuck, I can’t handle it anymore. I think I can cum by simply humping the air. I hope this thought never crosses Mistress’s mind… I wonder what she has in store for me. She’s been acting no less excited during the whole week. I hope it’s not going out in public in full fem. I’m not ready. I don’t think I’ll pass. Is it HRT? She’s been teasing me with hormones for months now… Ah, as long as I cum I don’t care anymore, really. Well, I suppose that was the intention behind hiding vibrators.”

5 minutes later, horny and dreamy, I reviewed my work outfit in the mirror. It was one of Mistress’s favourites. White short-sleeve tight-fitting turtleneck top, red pencil knee-length skirt, white 4-inch court shoes, red bead necklace, and red horn glasses. She also loves it when I wear a red bra underneath that top, the way it skittishly complements the look. I wanted to please Mistress as much as possible today so obviously I wore one. Delighted with the result I started working. Around 2 hours later Mistress knocked on my door.

‘Morning, Emily. Have you seen my blue yoga pants?’

My clitty painfully twitched once again. She was wearing only panties and a sports bra. Most certainly, to tease me. Her beautiful curves in all the right places, her perfect C-cup breasts, her little tummy which only complimented her gorgeous body, her effortlessly feminine elegance, her hazel eyes somehow always from above even though I was a couple of inches taller, so powerful and, ironically, so comforting…

I stood up, curtsied, and replied,

‘Good morning, Mistress. Yes, I believe I put them in your closet after doing laundry yesterday. The second drawer from the top.’

‘That’s a T-shirt drawer, Emily. The third drawer is for workout clothes. It’s not rocket science.’

Damn it. Out of all days.

‘I’m sorry, Mistress.’

‘Don’t be sorry; be better.’

‘I will, Mistress.’

‘Oh, you’re so adorable when you’re sad. Love the outfit, by the way. So sexy,’ she said as she approached and swiftly kissed me on the lips. ‘I’m gonna head out to the gym now. I’ll have the usual when I’m back.’

‘Of course, Mistress.’

‘Oh, that pedicure appointment you have tomorrow? I moved it to 3 p.m. today.’ That was far from good news. Tomorrow would have been not too bad, but now I had to endure the whole pedicure humiliation with my clitty aching against my cage.

‘As you wish, Mistress,’ I replied. ‘May I ask, what will be the plan for today?’

‘Just finish up everything and be at my disposal by 5 p.m..’

‘So you do have something planned?’

‘A well-mannered lady knows when to curb her curiosity and to just go with the flow’, she said mysteriously, leaving the room. What does that even mean?! By the way, certainly, don’t “go with the flow”, ladies.

This brief talk reminded me how a couple of days after that first Zoom call in a semi-transparent blouse, there was another work meeting where I foolishly decided to disobey my Mistress. I was wearing my boy clothes when she suddenly entered the room. She was supposed to be sleeping, but she had an early manicure appointment that I had totally forgotten about. She said nothing. In fact, she didn’t talk to me at all for the whole day. Later that night, however, she gave me a hard paddle spanking of 56 strokes (an extra 6 for me losing count a couple of times as I was thanking her for my punishment out loud). But most importantly, that was the last day I saw any boy clothes in my closet. From then on, Mistress kept them in a locker under her bed, handing them out to me when needed. Eventually, she just donated it all to charity and made me shop for clothes only in the women’s sections of online stores. Thank God we live in a modern age of unisex clothing. Still, searching for the least feminine-looking clothes was a chore, especially summer clothes, jackets and coats. Actually, what I learned is that women’s pants are much more comfortable and well-made… Well, anyway, as you can imagine, since then, no Zoom call has gone by without me discreetly adjusting my skirt or trying to gently wrap my blazer to cover my “breasts”.

When I finished working, it was time to get dressed for my maid duties. I didn’t have a lot to do around the house, but, again, Mistress’s good mood was of particularly great importance to me that day. So I selected her favorite outfit again. And what an outfit it was. As with every maid outfit I had (of which I believe there were 5 back then), it started with an overbust corset. I wouldn’t be able to zip any of the maid dresses otherwise, Mistress made sure of that. I think it was 26.5 inches back then. Now it’s down to 24, and Mistress and I are as proud of this number today as I was back then, staring at my tiny waist in the mirror, posing, and checking for loose laces. Next were black stockings. I would have preferred to pull them up before tightening the corset, but the corset had garter belts, so I had to struggle a bit. Once the stockings were up, I took the dress from the hanger. I definitely saw why Mistress loved it so much. It was an off-shoulder satin mini dress with a white roll-collar neckline and a black bow at the decolletage, little spaghetti straps, a tight-fitting boned bodice, and an a-line skirt with a ruffled organza underlay… It was beautiful. With my black stockings, white organza gloves, black rose choker, black hairband, and black 5-inch platform sandals I looked stunning. And I was aroused to the point of it being barely manageable.

I heard Mistress coming back from the gym we had in our basement, so I had to stop admiring my reflection in the mirror. I touched up my makeup, and I went down to the kitchen to prepare breakfast. Black coffee, scrambled eggs with avocado toast, green apple sprinkled with cinnamon for Mistress, and a carrot smoothie with avocado toast for yours truly. Back then, I was still on a diet, nearing 150 pounds. Which was a pretty healthy number for a 5’9 guy, but Mistress still wanted me to “watch my figure”. And as much as I hated being on a diet, I really appreciated my ever-reducing body weight when tightening my corset every day.

I was serving the table when Mistress came back from the shower, drying her gorgeous black curly hair with a towel.

‘My, oh my, someone’s dressed up. What’s the occasion?’

‘Well…’ I hesitated.

‘Haha, I’m just messing with you. But no, seriously, you look very pretty.’

‘Thank you, Mistress.’

As we were enjoying our breakfast, we chatted for a while about mundane work stuff. Then Mistress said,

‘Your roots need a touch-up.’

‘Do they?’ I said, caressing my shoulder-length strands.

‘Yes, Emily. A girl should be aware of such things. I’ll schedule with Helen for next week. Should we go with platinum blonde?’

‘Errm… Well, Mistress, I think my current shade is already feminine enough for it to be rather difficult to hide…’

‘True.’

She paused for a bit.

‘Hiding all of it has become too much of a chore now, hasn’t it?’ she suddenly said. ‘I mean, it’s not like you lead the life of a man who has a sissification kink. Not anymore, at least. After all our… “explorations” this year, it’s more like you’re living a sissy girl life while occasionally pretending to be a man, don’t you think?’

Of course, I’d thought about that. Or rather, that thought occasionally popped up in my head, and it scared me. It was too hard to contemplate. All of the shades of my new identity brought too many conflicting feelings that I was not ready to accept or rationalize. And so, when Mistress brought it up, it made me feel unsettled for a bit.

Seeing me gloomy and confused, Mistress softened up,

‘You know I love you, James…’ I raised my plucked eyebrows. I hadn’t heard her call me James for a very long time.

‘And I’ve grown to love Emily so much as well,’ she continued. ‘Makes me wonder who I love more… Haha. OK, thanks for the breakfast. I’m off to work. Don’t vacuum from 1 to 1:45, I have a call scheduled.’

And off she went. The ways she plays with my mind… Deep in thought, I proceeded to my house chores, contemplating, among other things, how it could be even theoretically possible to style a platinum blonde bob in a way that doesn’t scream “woman”. Thankfully, fulfilling sissy maid duties can certainly help drift away from anxious thoughts. I turned on the “This is Ariana Grande” playlist on Spotify (only ultra-feminine playlists when doing chores was another one of Mistress’s rules) and checked my notes. Cleaning the kitchen, dusting and vacuuming the living room and the second-floor hallway, ironing some of Mistress’s clothes after yesterday’s laundry… just enough to be on time for my pedicure appointment. Although 5-inch heels didn’t make it easy, Mistress’s rigorous training was paying off: I was prancing around the house with ease.

Nothing too exciting about the chores, really, so meanwhile, let me tell you how it all came down to this. As you can imagine, I was always fascinated by feminization and sissification. This fantasy was like a drug to me. But in a good way, I guess. I had a couple of dresses, some lingerie, a couple of toys, I had some fiction, games, and porn saved in my bookmarks, and I was pretty comfortable within the walls of my pretty sissy dreams. Shame, doubt, and fears—of course, I had all that as well. That’s why it took me six months to open up about my fantasies to Elizabeth. I came out, so to speak, in August 2021. She handled it surprisingly well. More so, she seemed pretty enthusiastic. She was always dominant by nature, plus she was bisexual and seeing me wearing lingerie in the bedroom wasn’t something she would aesthetically (or sexually) object to. Besides, I was far from a manly man to begin with, both in my interests and my appearance. And she liked that about me. Yeah, as I’ve already mentioned, I’m the luckiest sissy girl in the world.

A month after I “came out”, we participated in Sissylover’s Locktober at my suggestion. Prior to that, I didn’t have much experience in chastity, but that’s when I learned the true scope of Elizabeth’s domination fantasies and desires. She was incredibly strict and completely unbending. Obviously, she had the keys, and I started pleading for a release by the end of week one. But the more I begged, the more I learned she was thoroughly enjoying having control over my orgasms and, consequently, over some other areas of my life. As new tasks were arriving, as I was sharing them with Elizabeth, she was becoming more and more captivated by how deep sissification could possibly delve into one’s being, to what extent a sissy might want to alter themselves during forced feminization, how much power a woman could have over sissy’s whole identity, and… by the fact that I wasn’t completely against taking it all to a whole other level.

When Locktober was over, the rate at which fantasies overflowed into reality increased dramatically. Elizabeth became my Mistress. I became her Emily. We didn’t know where it would lead us, we didn’t have an end result in mind. We just knew that we both enjoyed this role-play enough to explore its limits. However, we agreed that Mistress would be the one dictating the pace of my feminization and sissification. I was supposed to trust her implicitly, and she was supposed to check, in her own elaborate way, that I was not too uncomfortable. To be honest, at the start, I wasn’t sure she understood what uncomfortable meant.

By December, I was spending nearly half of my time at home in heels, skirts, and maid dresses. By January, watching makeup lessons on YouTube had become a part of my daily routine. In February, we married, and a week later, I had my first ruined orgasm using only a vibrator. We also agreed that Mistress would be able to see other men (one-night stands only). Considering my new drifting identity, I was rather surprised that between February and October, she’d only been with 4 guys and 1 girl, and even then it was mostly “for the sake of adventure”, as she called it. Despite my worries, she kept telling me that I satisfied her sexually, just not in the ways a normal man would. Her pleasure was my pleasure, so I gotta hand credit to myself where it’s due: her sexual satisfaction was my priority in bedroom and I used whatever means I had available. Naturally, most of the time my clitty was not an option. In March, we moved into a new house where a small guest room would be decorated and furnished to fit my new lifestyle. It was also Mistress’s birthday, and I got her a luxurious spa reservation for 2 days (which I attended with her in boy mode to her chuckling disapproval). On top of that, I got her some expensive premium vibrators, which she had been eyeing for a couple of months. By the way, after those gifts were first played with, I don’t think I ever used my clitty for her sexual pleasures. Well, I literally brought it upon myself.

In April, I got my first laser hair removal, as well as hair and pedicure salon appointments. Also, my ears were pierced—two holes in each earlobe. In June, I started facial hair electrolysis, and my work dress code was introduced… and that incident with boy clothes happened. In July, she insisted on weekly anal stretching and deepthroat blowjob training, which almost instantly turned into a twice-a-week occasion. In August, my first public outing dressed as a girl occurred. We went to a shopping mall and visited a couple of stores. I tried on several outfits; we even bought some makeup at Sephora. And though Mistress kept telling me that I looked beautiful in my wrap flower sundress, that my posture and stride in my 4-inch wedge sandals were almost perfect, that my round feminine sunglasses complimented my soft facial features, that my curled blonde bob was so dainty and pretty, and that no one could tell I was not a girl—that’s the first and only time when the “uncomfortable” line was drawn. I didn’t know what it was, but I just felt really anxious and overwhelmed, to the point where I didn’t have to say anything. Especially when we went into a women’s bathroom. I just froze there, washing my hands for what seemed like 5 minutes. She saw it, felt it, sympathized, and after that, she didn’t propose going out in public in full fem for a very long time.

In September, on my birthday, the first birthday I spent as Emily the girly sissy maid, apart from some new lingerie, Gucci lipgloss, Gyvanshi perfume (and new Nintendo Switch Joy-Cons), I received a tiny inverted steel chastity cage. At first glance, it looked like a terrifying appliance. It did make me feel rather excited, though, that it would make my clitty look practically non-existent. I spent the rest of the month trying to get used to it, wearing it for a couple of hours a day, and I was pleasantly surprised that it was fairly comfortable—if not more comfortable than some of the plastic cages I had. The downside was that during Locktober, I would have to take it off every other day to clean it up under Mistress’s watchful gaze. And though it was all rather manageable, by October 1st, I still had no idea how I would be able to spend a whole month wearing this cage. Well, when your Mistress is as determined as mine…

And so, on October 31st, 2022, I was enduring the last hours of a whole month in that crazy little chastity cage. No releases, no ruined orgasms, no edging. I didn’t even touch my clitty for the whole month as Mistress insisted she would clean it herself (words cannot describe how much I love her). I wish I could say that by then I had forgotten how it felt to touch my clitty and how to masturbate, but I would be lying. I very much remembered, and as I was vacuuming the second-floor hallway to Ariana Grande’s “Positions”, a beautiful off-shoulder mini dress swishing when I moved, 5-inch platforms clicking against the floor, black stockings caressing my legs when they rubbed against each other, there was nothing in the world I wanted more than to unlock that cage and jerk myself off to oblivion.”

End of Part 1. Read Part 2 here

Want to follow in Emily’s footsteps? Tell me about your dream sissy life…

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