Sissy Training 101: How to be a Sissy
While it’s common for many men to experiment with different levels of crossdressing from dressing in drag to wearing a girlfriend’s thong, exploring the sissy fetish through sissy training takes it one step further. Not only do you have to be adept at crossdressing, you crave becoming feminine in order to be sexualized and be a source of pleasure.
Sissy training is a continuous journey, but one that you can take step by step. While this blog will continue to delve deeper into sissification and how to be a sissy, this post can help you as a first step.
Types of Sissies
While there’s no one right way how to be a sissy, having an idea of what type of sissy you are may help guide your journey. We’ll look closer at each type of sissy in future blog posts and what sissy training entails for each!
Bedroom Sissy
The Bedroom Sissy, as the name implies, engages in elements of sissification or even just mild crossdressing for sexual arousal. This may be as little as wearing thongs and stockings during sex to full-on sissy anal penetration. When they’re not engaged in sissy play, though, they revert to near-total normalcy.
Forced Femme Sissy
The Forced Femme Sissy likes to engage in a type of BDSM feminization that typically involves humiliation and degradation as a man is “forced” into acting or dressing feminine.
Sissy Maid
The stereotypical Sissy Maid is motivated by servitude to others and a traditional BDSM submissive role. They may literally dress as a French Maid, or not, but sissy training and play with them involves fulfilling various tasks for their dominant in order to receive a typically-sexual reward. Punishment may also be a significant part of Sissy Maid training.
Sissy Slut
The Sissy Slut, often also referred to as a Sissy Bimbo, is very self-driven in their sissy training to continue to be as slutty and feminine as possible in order to pursue their one true goal: worshipping cock. Whether it’s the cock of a mistress or a dom, this sissy wants to wear the skimpiest lingerie with their makeup gun set to whore.
Where to Start with Sissy Training: Buying Panties and Thongs
While you may want to jump right off the deep end when starting sissy training, buying your first pair of panties is a sissy rite of passage. You’ll also be able to tell pretty quickly if you’re just into the fantasy or the reality depending on if you feel euphoric slipping them on your first time.
Depending on what type of sissy you are, try to find the girliest or sluttiest panties as possible. Buy a skimpy thong or g-string or a pair of lacy, backless panties. Personally, I feel like sissies should always try to be as slutty as possible.
FYI, in terms of sizing you want to go at least one size up from your traditional men’s size. You may want to go two sizes up for g-strings or thongs with a very skinny string or side to them. There are also a plethora of girly thongs made for men from companies like X Dress.
Next Step: Sissy Accessories
If you’ve felt a rush of joy after slipping on your first thong, you’ll be wondering where to go next with your sissy training. I recommend trying to build your sissy look and persona one step at a time so you can continue to refine your look and respond to what you like. However, these are some fun sissy accessories and items to start playing with.
- Lingerie: after building up your panty and thong collection, a sissy needs their first set of lingerie to feel more feminine. Buying a traditional lingerie set with stockings, a garter belt, a thong, and a bra will get any aspiring sissy into a girly headspace.
- Wig: a wig for me was what really helped take me from a boy crossdressing into a sissy girl mindset. Plus, a different wig makes it easy to transition to different styles to be a goth bimbo one day and a girly blonde the next.
- Heels: a tall pair of Pleasers or other stripper heels will definitely make you feel like a slut as you practice your seductive walk. For women’s heels, add 1.5 sizes to your male shoe size.
- Press-On Nails: easy to apply, a set of long, pink nails from the drugstore will make your hands less manly and more feminine. Be sure to have some nail polish removal handy to make removal easy.
- Temporary Tattoos: a slutty tramp stamp or temporary tattoo right above a caged clitty is sure to be a turn on for you and whoever you’re playing with. You can find many naughty options on Amazon.
- Jewelry: buying a pair of large hoop earrings for non-pierced ears, a skanky fake septum ring, or a cheap, fake gold necklace will help to add just an extra touch to a sissy’s favorite whore look.
Sissy Shaving
Sure, sissies can absolutely be hairy and there’s no “right way” to be a sissy. However, in addition to it being a sissy tradition to be basically hairless from the nose down, having bare smooth legs that are soft and lotioned puts you right into a feminine sissy space. Plus, seeing your legs without hair for probably the first time, since you were a kid, can make them feel like new legs for your new sissy life and not your boring old, hairy man legs.
Many new sissies worry about what people will think, particularly if they are on the hairy side currently. After sissy shaving on and off for years now, I can assure you no one is going to notice in your everyday life. Many men shave these days. If they do bring it up, you can say you’re doing it for athletic reasons, you’re starting to work out and want to get a better look at your muscles, or even just that your hair has been itchy and chafing.
Makeup
Makeup is an advanced part of sissification because it takes skill and practice. From my sissy journey, starting to wear makeup, along with wigs, really helped make me feel hot and feminine in a new, sissy-type way. During sissy play, a former partner put lipstick on me for the first time, and seeing myself in that feminine way gave me this warm, beautiful feeling of joy. That moment marked a turning point for me from just playing around with lingerie and feminine things to wanting to try to be as feminine as possible.
Experiment by buying one or two cheap makeup products at the drugstore and see how it makes it feel. After that, look for some sexy makeup tutorials and try following along!
In future posts, we’ll dive deeper into advanced sissy training topics like getting into the sissy mindset, behavioral feminization, toys like chastity cages, and, of course, worshipping cock! I hope that this guide will help you take your first steps toward becoming a sissy!