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A Beginner’s Guide to Becoming a Sissy


A Beginner’s Guide to Becoming a Sissy

I am frequently asked about training ‘sissies’, which is one of my favourite kinks—forced feminisation. Just for those who are unaware, a sissy is a person  (usually a man) who adopts feminine-like behaviour to the extreme, and takes part in stereotypical ‘feminine’ activities, often within the context of BDSM. It takes a lot to become a true sissy but this is a short ‘beginners’ guide that I have put together to help those who want to become a true sissy. Let’s take those first steps into sissidom together.

1.  Personality

Number one on my list is personality. I have seen so many sissies who just don’t have the correct attitude. need to adopt ultra-feminine behaviour. To help with this, I usually make my girls watch films based on the lives of transvestites first. A quick search on Google will pull up quite a few. This is just so you can see what it generally is like. Keeping a diary also helps by keeping those emotions at the forefront of your mind. Women are generally more emotional than men so this conditions the mind to become more feminine. It also helps to choose ‘womanly’ activities over the more stereotypical male ones. Maybe take up a form of dancing, or fashion design or baking is another popular option. It is also considered wise to remain in chastity whilst training. A number of devices can be purchased if this is required.

2.  Hair

If you are already blessed with long, beautiful locks, then lucky you. However, most beginner sissies do not have this luxury and have to find a quality wig. When choosing a wig, try to buy it in a store and it is also always preferential to choose a quality-made wig over a cheaper one. This is because the look, feel and movement of the hair will be much more realistic. Choosing a colour that suits you is also very important. You can do this by trying on different colours in the shop until you find the perfect match. The hair style is also important. Many wig specialists will be able to style the wig in the store to suit your face shape and personal style.

tumblr_ncihl6Yaxl1tlwpboo3_12803.  Beauty

Beauty is in the eye of the beholder but if you have heavy, masculine features, makeup can really help to drastically change how your face looks. It can make your cheekbones stand out, slim your jaw line and nose and enhance your best features. It really is amazing. The core of any beauty regime is always the skin. If you have good skin, then you can work on the rest. Be sure to cleanse, moisturise and tone daily with quality products. There are many makeup tutorials online for transgender ladies which will also help sissies hide their more masculine features and enhance those beautiful feminine ones. Personal hygiene is also very important so be sure to shower or bathe as regularly as needed. And don’t forget your mani-pedi. Having a manicure and/or a pedicure really makes you feel ‘put together’. It also adds a very feminine touch.

4.  Clothes

Last but not least … clothes: the one thing that really makes a sissy. Some of my girlstumblr_ncihl6Yaxl1tlwpboo4_400 had brilliant fashion sense when they came to me. Others, sadly, did not and required much effort on my part to become what they are today. It is good to start with the undergarments. I think some nice pieces of lingerie such as satin panties or a lace bra really make you feel feminine. But ultimately, you are going to want to compact the panties and fill the bras. Breastforms are something you wear to shape your bras and provide breasts without the need for surgery. They also come in different sizes which is very useful. Vee strings are something I learnt about more recently but basically, they enable the wearer to tuck away any ‘unladylike’ parts whilst allowing the user to pee sitting down like a lady. Some of my girls have even employed the use of a waist trainer to accentuate that desired feminine waist. Ultimately you want to choose the best style for your body shape. Styling for your body shape takes time, practice and lots of effort. Shoes are the ultimate feminine weapon. The beauty of a high-heel never goes unnoticed but again, walking in these can take time, practice and effort. This is something you definitely have to practice. I advise to start with a low heel and work your way up to the desired height.

There are so many tutorials online to help with sissification, I have many of them on my Pinterest so feel free to browse and contact me with any questions.

Images courtesy of Mistress Winter
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Mistress Winter

Mistress Winter is 23 year old financial dominatrix and cam model from the UK. A recent university graduate with a degree in a science related subject under her belt, her main interests are now animals, gaming, money, photography, reading and tea.


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