Sissy Beginnings: Where to Start?

In terms of being a sissy – sissy girls always want to know where to start. Most are hoping I would say go buy your first pair of panties but that is actually ground zero.

Sissy Training with Mistress Lillith

If you haven’t even done that how can you POSSIBLY say you are interested in sissification? You can’t even classify your curiosity as fem curious or sissy if you have never slipped into a pair of panties. If you haven’t tried on a pair of panties, never felt that smooth silky fabric run up your legs and hug your hips…if you don’t know the luxurious feel of panties wrapped around your clit stick – you aren’t a sissy…you’re a curious panty whore. You are so far behind the learning curve right now and You need to catch up.

Go buy yourself a pair of panties at the store, order them online…or do whatever an incredibly high percentage of sissy trainees do – and steal them from someone you know. So many are prancing around in a pair of their mothers stolen panties or stretching out their wife’s panties. They know the feeling, and they know they want more. THEY are prospective sissies.

You wouldn’t walk into a class room without at LEAST a pen and paper, don’t come to me asking for sissification or sissy training without at the VERY LEAST having a pair of panties . Id consider you just a some dumb stroker boy in a PRETEND bra and not take you all that seriously. It really is the VERY least you can do.

Even panty sluts that don’t label themselves as sissies – know that panties are a must.

Only AFTER you’ve experienced wearing the panties can you move on to other things. While I still find you wearing your first bra or negligee or full set of sexy lingerie too pedantic and to ‘inside the box’ for my liking, I can respect that its usually because I’m just more experienced than they are and will walk them through it – that is why you come to me for your sissy training needs in the first place. SO yes, I’ll walk you through your first full set up on lingerie. BUT, it will be quickly because I’d want you to have an array of different outfits to try on. I love nothing more than a sissy fashion show. I’ll cue the music and I’ll even record it for later fun and exposure (all with consent my dears. ? You KNOW how I am about consent)

Maybe the sissy fashion show SHOULD be your first introduction as a sissy.

Your style of clothing is going to tell me so much about your personality and who you are. The changes between and how you walk that sissy catwalk are also going to give me some insight into you. I like to have fun with it and that is a fun, lighthearted way to fill each other out

As far as where to start AFTER your panties – I would say buy clothes. Go on a shopping spree. If it fits, it’s bought. If you don’t know where you are going as your sissy train leaves the station, you will want to make several stops and as many as you can to narrow it all down.

If you aren’t quite that serious about it yet and just want to dip your nylon covered painted toes into the water to test it – you’ll want to do some research. What kind of sissy DO you want to be? What about the femme lifestyle interests you most? Is it the mannerisms, the fashion, is it…the men? Are you into being of service to dominate women but like the costumed/uniformed look? What kind of looks DO you like?

Doing a tiny bit of leg work on YOUR part will enhance your sissy experience from the very beginning and will give you an idea of where to start and grow from.

Of course,…being an experienced sissy trainer I take all those green to sissification and turn them into the pretty pink frilly sissies…sometimes with a tad bit of forced fem. It is in your best interest.

You’ve got your panties…you know the feel. You know that is the start for YOU but not the beginning when you start to seek out training or seek out ways to grow your sissy lifestyle. The beginning is when you take a snap shot of who you are and what you like, the beginning is when you find yourself looking up outfits and clothing for YOURSELF, the beginning is trying to figure out if that sexy little negligee on the wish app will fit you – and you simultaneously wondering how to measure yourself in the first place.

What kind of sissy do you want to be? Close your eyes and picture her – and I’ll be there to help you perfect her and bring her to reality.


If you are interested in some sissy fun you can check out my sites and You can even enroll in my online sissy school training on niteflirt. You can also follow me on twitter @mistresslillith. Questions, comments or topic requests can be posted below in the comment section 🙂

Leave a Reply

Your email address will not be published. Required fields are marked *