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.

6 thoughts on “How should a Sissy Masturbate?”

  1. I am not a ” MAN “, just because i was born in this stupid, dumb-ass male body does not mean that I am a man. I am a sissy faggot, and I will never be attracted to, or get pussy . I hate women’s pussies, I’m only good at sucking cock. I have no other use, I am in a wheelchair, but that only makes sucking cock easier because I am at crotch level.

    I love wearing women’s clothing, especially lingerie, and I HATE wearing men’s clothes. I want only to please my mistress, and only her, but like I said my clit-dick is useless to her. I want to do the household chores, and look right for mistress and her company. I am gay, and only want to suck mistresses male company cock. I have no other skills except
    a sissy maids chores, wearing women’s clothing, and sucking cock.

    1. I have been a sissy all my life but now I have the courage as my wife left me my kids moved away and I am all alone.
      Followed your instructions and shaved all my body hair. Should I trim my eye brows ?
      As I am starting to be a sissy now please give me a few tips.
      I am so excited.

      1. I love taking orders from my mistress but I haven’t got one. I have a house help . Should I confide in her and beg her to be my mistress ? I want to obey her but she is shy to order me around I suppose.
        Any suggestions ?

  2. The target may have been hit here, the nerve scratched Mistress. I have long understood intellectually that I must be transformed from being a male who jacks his cock just to ejaculate into the air TO being a non-male panty-wearing sissy who learns to self-pleasure by pillow humping with the new goal being to make ‘panty messes’—I foresee the End of Ejaculation.
    Can this be trained over time?

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