Category Archives: Sissy Masturbation

How should a Sissy Masturbate?

How should a sissy masturbate?

That is kind of a funny question isn’t it? Perhaps the question shouldn’t start out as HOW, but rather, MAY a sissy masturbate.

I would say first and foremost you would need to obtain permission before any sort of self pleasure. Most mistresses and sissy trainers will have you under lock and key, having that sissy clitty locked away in chastity, others will have you on a strict cum restriction schedule.

BUT,

SHOULD you actually earn permission – there is a special way that sissies should masturbate.

Guided Sissy Masturbation with Mistress Lillith
Guided Sissy Masturbation with Mistress Lillith

You need to make sure you are dressed in the proper sissy attire. Your lingerie, your sexy little chemise, whatever puts you into that sissy subspace. You don’t get to stroke like a ‘mans-man’. You aren’t a man.

You must add extra layers of lipstick to feel a little more femme, a little more sexy.

Put on some music that makes your hips sway side to side. I want you to really take your whole sissy self in by examining yourself – head to toe in a mirror.

Now, when it comes time to enjoy yourself and engage in some sissy masturbation, you should know that you don’t get to clasp your hand around that sissy cock and stroke, oh no.

You treat it like the sissy clitty that it is and you masturbate just like a girl would. Using your fingertips and going in a nice circular motion right on that clitty.

That is just the start of it. Of course, it is preferable that you only engage in sissy masturbation with your Mistress or Domina. Obviously she will give you further instruction as to how to get to that edge and spew that sissy spunk if you are permitted to do so.

Remember, you are a sissy. You are a girl. You must masturbate like a the sissy girl that you are.