How to Train your Sissy

Sissification is a comprehensive transformation process that involves clothing, makeup and behaviour to fully focus the subject on their feminine side. You might think that’s just cross dressing, however, sissification goes beyond the cosmetic. Sissies wish to experience being treated physically or psychologically in a (stereotypically) ‘feminine’ way. For many men this exploration allows him to honour his more feminine characteristics, reconnect with parts of himself toxic masculinity has forced him to supress, and have a genuinely transformative journey. And unlike cross dressers, sissies have to train!

This training can be done solo, or with a partner or supportive friends, and the best thing is, it can be instrumental in creating fun scenes, and of course, the offer of punishment, ‘funishment’, and rewards. There are some general things that any sissy can do to improve their femme identity – like posture, voice training, and movement – but there are also an array of specialised ‘lessons’ depending on the type of sissy you like to be, or the service you’d like to excel in.

Types of Sissies

Maid: 
This sissy takes pleasure in domestic serving, but this service is not just about obedience. It’s an art form in which they take pride. From their freshly ironed uniform, perfectly placed hair, and make-up that enhances every feature, they move with smooth efficiency ready to address any needs.  

Slut: 
This seductress of a sissy enjoys playful promiscuity, and embodying the fluidity of sex, connection and intimacy. These sissies are often hyper-feminine, and unapologetically indulge in filling their newly discovered holes with any of the toys from what is sure to be a vast collection. 

Slave: 
Unlike other sissies, the sissy slave’s focus is on full service. They will serve in whatever way is required by their Mistress/Master as this is an act of worship, transforming everyday tasks into acts of spiritual surrender. 

Chastity:
Chastity is not so much of an identity, but a common way to achieve part of an identity. It’s not uncommon for sissies to find a sense of liberation in chastity. Relinquishing their masculine sexual freedom in exchange for an exposed hole gives some sissies an extra sense of the feminine. I mention it here, as it is something that will require a little training.

Pre-Plan Training

Primarily work out the sissy type you’d like to embody or create. The training required for a maid will be much different from a bimbo/slut type. Work out any resources you need for your training and have them prepared. Once training begins, you don’t want anything slowing down your momentum.

Affirmations

Psychologists have long recognised the power of words and self-talk. When used consciously and regularly, affirmations can create a pathway of positivity that supports mental well-being and encourages behavioural change over time. They can be an important part of the sissification process as they are designed to build a positive and resilient mindset that can counteract societal demands and expectations, while creating a new foundation on which new values can stand.

Sissy Hypno

Sometimes a controversial topic, Sissy Hypno is a genre of porn developed to ‘hypnotise’ (mostly) men into feminisation. For some sissies without partners, hypno uploads work as a type of solo training with online guidance. This content is gaining so much popularity there are specialist Sissy Hypnotist content creators and influencers, some of whom are in the top percentages on their platforms. But there are also reports of high rates of content addiction from these consumers – some believing the hypnosis is affecting more than their femininity.

Incorporating Training Into Your Play

Keep your training fun. Keep it joyful. It should never be a stress, or something that zaps your energy. 

The basis of sissy training begins with building a wardrobe that embodies femininity. The sissy’s wardrobe will always have a place in any play, but one way to focus on it is through a thorough inspection. Slow undressing, compliments and critiques on twisted straps and symmetrical panty lines, encouragement and correction of posture and poise throughout – an excellent start to a scene. And of course all good girls loves some pretty gifts, so using lingerie as a reward for progress, or a goal to work towards can be an enticing game.

Training can also be specific to the type of sissy you’re wanting to encourage. For maids, it can be fun to play with sensation while they practice their deportment by walking with a book balanced on their head – deploy zaps, spanks, or tickles each time the book drops. For the sluts and bimbos, much of the training is sexual, and includes anal training – stretching the anus to comfortably take bigger dildos, toys, and body parts like the fist – and oral training, much of which is supressing the gag reflex enough to allow for deep throat and face fucking. As more passive players, cucks are fantastic to tease. Denial is one of their core erotic themes, so anything you can devise to over or under stimulate your cuck will provide some very useful training, particularly in regards to their ability to achieve sub space during a cuckolding.

Embracing your feminine side requires confidence. Affirmations, pretty lingerie, and a flirty time can help boost your self-esteem, but solid confidence comes from within and the little dopamine rush that comes from a perfect wing line is no match for just feeling great about you. Ultimately sissification is all about creative self-expression and personal discovery. Have fun and enjoy the process and in time your sissy persona will reward you with a lot of fulfillment.