This is a follow on post from a challenge I am doing for the months of September and October This is a follow-on post from a challenge I am doing for the months of September and October. You can find the original start to this thread here https://lovenselife.com/article/1694452347500

Seriously ladies' what's the deal with your clothing, whys there no pockets?!!??

It has been the most frustrating thing of my time in chastity thus far, that I literally have to carry everything that I need, as girly clothing has no pockets or ones which are completely unusable.

Part of my time in chastity and to embrace Sissytember was to undergo some form of feminisation. This is part of the power play dynamic of being a sissy, whereby the dominant will dress their submissive in extremely girly clothing to emasculate, humiliate or degrade them into servitude. Because let's face it, it's hard to be dominant whilst wearing a pair of pretty panties. Also please note that I haven't used him or her here because a girl could also be classed as a sissy if they were to share similar traits or put into similar roles such as a French maid, or secretary.

Sissyification differs from being transgender in the sense that there is always the choice from the sub to reverse the process or in extreme cases accept becoming a woman and start chemical or physical changes to themselves. Whereas a Transgender has already made the decision to change gender and has taken physical steps to start the process

Feminisation is the first part of becoming a sissy, but as the sub is encouraged to take on an exaggeratedly feminine role in the power play, they will be tasked with more activities by their Dom to mimic feminine behaviours. For instance, training their ass as a pussy and learning to cum from that stimulation, what is commonly known as a sissygasm.

To start the process off a few ground rules were set to force the feminisation, these were,

+Girly panties will be always worn whether inside or outside the house and if necessary, under boy clothes.

+No boy clothes are to be worn inside the house and heels must be worn, except where there is a need for health & Safety.

+You will always be dressed for sleeping

On top of this my Keyholder Goddess can assign additional tasks to increase the level of feminisation, such as wearing certain outfit or wearing makeup.

Now I know what you're thinking where is he going to get outfits which will cover an entire month, well I had some of them from my previous relationship where I was encouraged to explore my sissy sub side. Before that I had dipped into sissy, because my Dom side really wanted a girl dressed as a French maid to do some chores for me, but I couldn’t find anyone to fulfil that role for me, so I ended up doming myself into the roll.

The thing that makes my keyholder giggle the most about the femisation, is the heels. Me and my Keyholder regularly speak on the phone, and I always get a comment from her when I start walking around the house and pass over a tiled or wooden floor. The clickity klackity of the heels is very distinct as I work on chores and tasks for my Goddess and I tell her that if we were together, she could always tell I was working by the click of my heels. It's when they stop you know I'm up to mischief. I have a selection of heels depending on my outfits, the worst being a set of ballet boots which just immobilise me, then some 6” platforms down to some 3” court shoes.

I have every sympathy for you ladies that wear heels because it is soooo hard. But I will say there is some benefits, it gives my legs a super work out walking around in them, I can reach things on the top shelf far easier now and they make my butt look fantastic. I will say though that come Monday morning after a weekend of being in heels, it does feel weird slipping back into flat shoes and I really didn’t think I would adjust to the heels that quickly, in some respects its quite scary. Big tip for any budding sissy’s or cross dressers out there is Gel pads for high heels by scholl are life savers and certainly make it easier to wear heels for longer.

The other thing I'm sure every lady would appreciate is the fact that all the loo seats in my house are down 😊. The chastity device does not allow me to pee standing up, so every potty break is spent sitting and certainly a forced feminisation act caused by the chastity. Now when I pee’d standing up I always thought I was a good shot, but how I was wrong, since being in chastity the toilet and the area surrounding it is far cleaner so something defiantly to note for those of you who live with a guy you are sure stands on the toilet seat and aims outwards XP. The situation has also made me consider the plight you ladies go through a lot more, public toilets are just awful, especially the ones in bars and can see why unisex toilets are just a bad situation for you.

But enough about toilets and onto the fun stuff, the French maid a thing of beauty, with a short skirt with enough ruffles to tease until there bend over and a flirty feminine aspect all defined in black and white. For a service sub like me, it is the perfect outfit. During my time in chastity whilst I'm carrying out cleaning chores, I must wear a maid's outfit, which my goddess can then verify using the chaster app system. I know she certainly enjoyed the thought of me on my hands and knees, scrubbing floors, with my dress doing a good job of exposing my butt as she played with cage using the diamo and fucked my ass with the hush. Jobs certainly take longer when you're having to stop every few moments to centre yourself as she talks about fucking me with a strap-on.

The Chaster task list decided I needed more feminine clothes this week too, as it tasked me with ‘shopping for lingerie’ and after a discussion with Goddess it turned into a full outfit. Bra, thong and even a suspender belt were added to the list before goddess topped it off with a new dress, apparently, I needed more colour in my life with a matching set. She wasn’t wrong and when it all turned up, she of course requested a photo, with the comment being great legs you need a pair of matching heels with that now Lol. Which answers the question why you ladies have so many pairs of shoes. XD But it's now become my working from home outfit and I thank my goddess for her encouraging me to buy it

Goddess continued to check on my outfits throughout the week as I took naughty verification photos for her through Chaster. With positive encouragement from her I certainly felt more at home being dressed sissy, than feeling forced to in order to complete chores.

A step on from the clothing is makeup, there are a few tasks where this is forced to be applied, from lipstick and lip gloss to eye shadow and eyeliner. Again, I now appreciate how much effort and time you ladies put into getting ready for us as eye makeup is hard. So, thank you all ladies for looking good for us 😊 I will say youtube is a godsend for makeup tutorials and really do make it a lot easier to get a look, just remember to take it off before bed to avoid the panda eyes in the morning. Lol and lipstick is such fun when your practicing deep throat training, as you can see from the ring around the cock how far you're getting down and I'm sure the boys would be happy with any girl/gurl who could put a ring around the base of their cock.

One thing myself and my Goddess did at the start was to come up with a name for me as my sub sissy self. As I switch from dom to sub it will help me to know that when I am referred to with my feminine name by Goddess or others, I know that I must assume my submissive role. Additionally, when I chat to my Goddess, she will be able to see what mind state I'm in by the way I refer to myself and will know what is a formal request from her submissive. The name we came up with, is quite good as it means hard working. For those who have voted on my lock or are in Chaster you will know what it I and I am proud of it, as it does cause a little flutter when Goddess uses it. 😊

The no Boys clothes in the house rule is frustrating, when I'm heading out for work or socially, I must get changed in the tiny cloak room just by the front door. It also means when you're heading home and just want to chill out and relax when you get in, you can't as you must instantly strip naked and jump into the outfit for the evening and heels. I also must get changed twice in the morning, once to get breakfast and get ready and then a second time at the door to get out the house, I now see why ladies take so long to get ready to leave the house with all the outfit changes XP. It certainly is taking a lot of getting used to, the transition between outside and inside the house.

The final note on this is something I did when I locked myself up at the start of the month and that Goddess can request at any time and that’s for me to apply a “Sissy” temporary tattoo just above my cage which normally stays on for 3-4 days before washing off. I catch it in the mirror at night and in the morning as it is quite prominent and it feels strange to be branded this way, I know I blush when I see it, I shouldn’t because I know it will wash off, but it just makes me smile that I'm someone's sissy.

If you got this far thank you for reading, Next week's post certainly takes a step up a notch in terms of me and my goddess’s dynamic so it's worth continuing to read for that.

If you have any questions about it all, feel free to reply here or DM me, I'm happy to answer most questions and share my experiences with you.

Regards

Rectitude