Sissy-guided Masturbation isn’t a subject that I’ve focused on discussing. Strange isn’t it? The girls certainly masturbate! But is sissy-guided masturbation the same as any other guided masturbation? Well yes and no! That was clear as mud, wasn’t it? Don’t fret, let’s explore sissy, guided masturbation!

Guided Masturbation

As it states, Mistress guides your masturbation. She tells you how to stimulate and when to stop, along with heaping on the tease. She may use fantasy imagery, or even watch porn videos with you,. Other ways to spice up your masturbation sessions is using commercial sex toys or DIY toys. Orgasm edging is very common in these types of sessions, as well as exploring various ways to masturbate.

Often guided masturbation sessions are not necessarily heavy on the D/s elements. No poignant power exchange, not what many would call “cock control”.

There are many who enjoy being instructed how to masturbate, even showing off their masturbation skills to us on cam. Sharing such an intimate experience with another is very erotic, and I always enjoy the show!  But also true is that Mistress guides your masturbation, as part of your submission to her. In doing so she exerts way more control, and the power exchange is palpable.

Sissy Guided Masturbation

So taking the elements above you can imagine sissy-guided masturbation would be similar and you would be right. Mistress guides, and sometimes there’s more. For those who identify as a sissy, being as feminine as they can be is often their goal.

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I know it’s a goal I have for all of my sissy gurls, cross-dressers, and trans women,I have the pleasure of knowing. Often sissy guided Masturbation is part of her sissy training.

Where sissy-guided Masturbation varies is the scope of the play. In an effort to be as feminine outwardly, there is often a strong desire to experience everything internally. That means using the parts of their body that can be used to penetrate. I’m being coy and I think we all know what I’m talking about. Anal sex, and even oral.  Some sissies include cock sucking training with their Mistresses. cocksucking training is a favorite way to encourage your sissy slut level!

Sexy Options WIth Sissy Guided Masturbation

With sissy-guided masturbation so many more options for play are at our fingertips. Some sissies want oral cock-worship sessions and training that sweet sissy honey hole to easily accept any grand cock. Mistress can increase the feminine experience, and submission to the Mistress by altering how the sissy masturbates. First with the frenulum rub, learning how to cum by rubbing her clit, not stroking a dick. The goal not to stroke like a guy but rub like a girl is often high on the priority list for Mistress and sissy.

To change your addiction to stroking that clit small steps are often needed, as mentioned above the frenulum rub. There are toys, not necessarily penis-stroking toys, remember: Often with sissies, the penis is gone, and hello to the clit. So teaching sissy to hump and rub and treat her nether regions like feminine ones is next level sissy guided masturbation. So vibrators and other toys made for women are used.

Sissy Orgasm

A sissy orgasm is an orgasm sissy has through anal (pussy) stimulation.  Playing with that sissy pussy to have a sissy orgasm. is a must-try for many sissy gurls.  Experiencing what it is like to be penetrated like a woman through strap-on play is an exciting and naughty way to feel and experience your femininity on a whole new level. Often sissy orgasms are facilitated through stimulation of her clit.

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Sissy Masturbation


Once the sissy orgasm has been achieved, going totally a hands-free orgasm is also an option for Mistress and sissy to explore. First, through increasing stimulation to that sissy pussy. Fingers first, small dildos. Learning how to orgasm through penetration and perhaps a bit of a clitty rub, then it’s an easy step to hands-free, clitty flailing (or permanently locked?) having whatever boy is left,  screwed out of her. There’s no longer a need to even touch that clit again.

Nipples, nipples nipples. many guys love nipple play, others are ho-hum about it. But, not true for the girls. I can’t remember a sissy, in my history pouting over nipple play. They may moan, or gasp perhaps, but no pouting. Enjoying making those nips puffy and sensitive!!

Reach Out And Explore Guided Masturbation Sissy Style

Of course, you don’t have to have sissy desires to enjoy guided masturbation, but if you didn’t have the slightest inkling, interest, or even curiosity about including feminine frillies with your masturbation why have you read all the way to the end? Don’t be shy or embarrassed, we understand. So gather your panties, bra, or your other feminine accouterments and have a sissy-guided masturbation good time, with Mistress.

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