What’s Inside A Sissy Men Training Kit?


Sissy men’s training kits, then, are an exhaustive array of mixed instructions and devices curated by specialists in the Sissy community.

Often, these are the masters or mistresses who had already trained countless sissies.


What_s Inside A Sissy Men Training Kit


These training kits are contemplated based on different, but similar objectives.

“making a man more feminine (delicate, soft, etc.)” or “making the sub more compliant.”

These goals can be adjusted based on the trainer and sissy’s discussions.

They will also be affected by the master and sissy’s unique circumstances.

Sissy men who want to start their feminization journey can also use these kits on their own first.



Sissy Men and Training


What_s Inside A Sissy Men Training Kit 


Sissy men training kits aid men who want to explore their femininity, specifically in connection to a fetish or kink.

Sissies are submissive men who want to be dominated through feminization.

Be wary though, to not misinterpret sissy men training as the same program some transwomen undergo to fully embody their womanhood.

While transwomen go through feminization to move, speak, and think like women, it’s to answer a psychological need.

Sissy men go through feminization for various reasons as well.

When it’s linked to BDSM, sissy men’s training kits are for sissy play and are followed by the bottoms to please their dominant partner better.


What_s Inside A Sissy Men Training Kit 


Sissy men’s training includes conditioning and roleplaying where the sissy gives up his power to the dom.

Training kits make these processes easier.

They’re like the starter pack every dom or sissy (if you’re training alone) can rely on to ensure they’re on the right path and are progressing.


Components of a Sissy Men Training Kit


What_s Inside A Sissy Men Training Kit 


A compilation of sissy tasks or sissy rules can already be considered a training kit.

In this guide, I’ll be talking about the more comprehensive kits that include more than just instructional prints.

A complete sissy training kit has:


Guidebook or manual

Feminine undergarment

Feminine clothes

Beauty Products



Sissy Men Training Kit: The Beginner


What_s Inside A Sissy Men Training Kit 


A training kit that introduces the must-knows of sissy play. If you’re a total newbie or have a few ideas about it, go for this collection.

The goal here is to get familiar with and slowly ease yourself into sissification.

The usual contents of the beginner sissy men’s training kit include common female items.


Guidebook or Manual


The beginner’s manual should have a list of terms often used in the sissy community.

This guidebook can also include a straightforward explanation of what a sissy should expect in his training.


Feminine Undergarment


Newbie sissies should start with average panties with simple designs and styles.

These undergarments are more focused on practicality and coverage and have little difference from usual men’s underwear.

The cut and fabrics are also similar to facilitate the transition.

It can be more snug in the crotch area.


Ladies’ boyshorts

Ladies high-rise briefs

Hipster panties


What_s Inside A Sissy Men Training Kit 


Feminine Clothes


New sissies are not expected to immediately start wearing clothes that are traditionally for women.

This kit may include simple dresses and skirts, but I do not recommend wearing them out in public yet.

If you plan to wear something in public as a sissy, start your training with women’s clothes that can also sometimes be considered unisex.





Fitted tops


Beauty Products


Cosmetics and wig selection require another in-depth field guide.

Generally, new sissies should know the essential makeup products and simply put on long wigs with natural colors.


Face Primer




Lipstick (can double ass blush and eyeshadow)


Men who have sensitive skin can simply use lipstick for color and baby powder in their first makeup experience.




New sissies have more pressing things to learn about before going to accessories.

Still, accessories polish the whole presentation, so a kit can have:


A jewelry set (a pair of earrings, a bracelet, and a necklace)

A purse

Legwear (stockings, cute socks, etc.)

Women’s flat shoes (ballet flats, mules, etc.)

Common and simple sex toys (small and subtle butt plugs, bullet vibrators, etc.)


Sissy Men Training Kit: The Intermediate


What_s Inside A Sissy Men Training Kit 


This kit features a more daring version of the previous pack, but not anything surprising.

It can also include exclusive crossdressing or sissy ingredients.


Guidebook or Manual


The sissy handbook will involve more detailed feminizing techniques and explicit instructions.

Manuals within the training kit can also involve detailed instructions on how to apply more advanced

feminizing techniques to himself such as sissy hypnosis or working with an experienced master.


Feminine Undergarment


What_s Inside A Sissy Men Training Kit 


Sissy panties will now come into the picture as a sissy may be versed in tucking.

These underwears are less focused on practicality. Instead, there’s an emphasis on visual appeal and the sensual feel of the cut and fabric against the skin.


Underwear with delicate or sheer fabrics like lace or organza

Thongs or G-strings

Strategically-cut bikinis



At this stage, a sissy can remain untucked and choose sissy panties that accommodate the crotch area.


Sissy or femboy panties with pouches

Sissy panties with spacious crotches


Feminine Clothes


What_s Inside A Sissy Men Training Kit


Clothing in this category should be more feminine-leaning. There will be few to no excuses when a sissy wears them.



Skirts, especially microskirts

Summer dresses

Beauty Products


By this time, the sissy should already be an expert in the basics of makeup.

More advanced beauty products help feminize the face or follow the crossdresser’s aesthetic.


Contour and Bronzer



Eyebrow pencil

Setting spray



There are many more makeup products to discover and experiment with so sissies should try a beauty product at least once.

When it comes to wigs, a sissy should know the different materials used to create the product.

The best wigs are made of real human hair but are often more costly.




What_s Inside A Sissy Men Training Kit


The aim is now to help the sissy have a more womanly presentation.

Aside from fashion accessories, intermediate sissies should also learn to use:


Silicone products to enhance the sissy’s “female” parts (breast forms, hip pads, etc.)

Bodyshapers (bodysuits, corsets, etc.)

Shaping bras (push-up, padded, etc.)


Sissy Men Training Kit: The Expert


What_s Inside A Sissy Men Training Kit 


Now is the time to play around and push boundaries.

If you’re looking to discover new aspects of sissy play, be open-minded about what you want and can do.

This category often caters to the more complicated parts of being a sissy and depends on the sissy’s

willingness to put more effort into his immersion and presentation.


Guidebook or Manual


Guidebooks in this section will answer the specific intention of the sissy and his master. It can be to be more kinky,

have a more immersive play, or combine sissy play with another BDSM activity.

For instance, a sissy may want to do a master-servant roleplay and present as a devoted sissy maid.


Feminine Undergarment


It’s time to pull all the stops and be acquainted with every hosiery material and lingerie at your disposal.

It’s also the time to incorporate items like harnesses, chains, and other BDSM elements in your presentation.



Fetish hot pants

Body jewelry


What_s Inside A Sissy Men Training Kit


Feminine Clothes


An expert sissy’s clothing will depend on his role within the play. It can also be the costumes the master requires them to wear.

Common sissy costumes are:


Sissy and seductive maid

Sissy nurse

Sissy warrior/servant


Beauty Products


A sissy should now know what products to use to match his aesthetic.

Be careful not to overdo it as well and to continue developing your makeup skills.


vrossdress with roanyer 




There are endless accessories sissies can use depending on what play they want to add to the main one.

These can include extreme sex toys such as giant dildos or unusual foreplay items like candy g-strings.

Presentation-wise, crossdressers can wear fake vagina pants, realistic female masks, or full-body silicone bodysuits.

They can also use silicone products related to other kinks, such as a pregnant belly.


Can I Customize The Training Kit?


crossdress with roanyer


Sissy men’s training kits are made to educate and help the sissy evolve.

As learning is different per individual, anyone can customize their own kit.

A dominant partner or trainer can also prepare a personalized training kit for the sissy.

The training kit’s contents will vary depending on the partners’ interests, comfort levels, and training goals.


Important Reminders


Crossdress with roanyer 


Having the most fun in your sissy training? Good! But don’t get too caught up.

What are your boundaries? How do you plan to communicate within and outside of the sissy play?

What safewords are you going to use? Be firm and chat about all of these with your partner before starting.

Above all is safety. Both of you should be watchful and take care of each other’s physical and emotional health.


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