What Is a Sissygasm (and How to Have a Sissygasm)

What Is A Sissygasm? (And How To Have A Sissygasm)

If you’re sexually adventurous or are looking to become a bit more sexually adventurous, then you might have heard the terms “sissy” and “sissygasm” in your research. 

But what is a sissygasm? 

And for that matter, what’s a sissy? 

Luckily, this article is a handy guide to all you need to know about sissies, sissygasms, and how you and/or your partner can have one!

What Is A Sissy?

Before we start talking about sissygasms, we need to make sure we’re clear on what a sissy is. 

Sissy is a term used in the context of BDSM, more specifically in the context of feminization, which is also sometimes called sissification. 

In sissification, a submissive male participant takes on a feminine role by acting like a woman, including my cross-dressing (that is, wearing clothes that are traditionally feminine). 

Men who like to role-play as sissies in sexual situations are typically (though not always) heterosexual. 

They are also distinct from transgender women; transgender women are women, whereas sissies are simply men playing a role for a sexual purpose.

Sissies are turned on by being treated as women sexually. 

This can include wearing lingerie and makeup, receiving anal sex, being referred to by a female name, and other things that involve them being treated as a woman. 

For some sissies, the enjoyment comes simply from this treatment as a woman while for others, it’s combined with other elements of BDSM like erotic humiliation, spanking, bondage, and so on. 

A fairly common example is a dominant partner humiliating the sissy for having a small penis, which is often called a “clitty” in the context of sissy play.  This sometimes includes wearing a chastity cage on the penis so that it’s impossible for the sissy to get an erection or to sexually stimulate themselves by touching the penis.

Some have suggested that the pressure men face in society to act in a traditionally masculine way is the reason that so many men enjoy sissy play to some degree.  Maybe or maybe not, but whatever the cause, there’s no doubting its popularity. 

Sex workers report feminization and sissy play as one of the most common fantasies of their clients.  If you’re interested in sissy play, you’re far from alone.

What Is A Sissygasm?

Now that you know what a sissy is, we can learn about sissygasms. 

Men who role-play as sissies often want to be able to cum like a girl.  This means being able to cum from penetration without touching their penis. 

On a physical level, then, a sissygasm is what’s also often called a prostate orgasm outside the context of feminization. 

However, for the sissy, it’s more than just that.  It’s a moment of the highest pleasure as a woman and the culmination of their sexual femininity, meaning that the feeling of orgasm is tied together with their feeling of being a woman.

The sissygasm isn’t always easy to achieve, and most sissies will struggle to manage it at first.  However, rest assured that it can certainly be done, and there’s plenty of video evidence available online if you’re skeptical!  

How To Have A Sissygasm

Achieving a sissygasm is often a challenge, particularly if you’re new to it, but don’t be discouraged!  The incredible feeling of that first sissygasm is so worth it, and you’ll get there eventually.


Before you get started, there are some things to consider. 

A sissygasm is going to include anal penetration, so you need to be clear about what this is going to be.  It could be a dildo or prostate massager that you’re using yourself, or maybe a strap-on dildo or a real penis used by your partner. 

If it’s a toy, make sure that you and/or your partner have access to it and are comfortable with how to use it.  Along with the toy, don’t forget lube! 

The anus doesn’t naturally produce enough lubrication for comfortable anal play, so lube is essential.  Without it, not only will you not have a very good time, but you might even hurt yourself, so don’t think you’ll be fine without it. 

You’ll also want to use an enema to make sure you’re clean, but either way, putting a condom over any toy you’re using will reduce the risk of any kind of infection.

When all the material preparation is finished, you still have psychological preparation, and this is just as important.  You can’t expect to simply thrust a dildo in and out of your ass and force yourself to cum. 

Above all, an orgasm happens in the mind, not the body, so take some time to get yourself into the right headspace. 

How you do this is up to you, but lots of sissies like to get dressed up in their sexiest, most feminine clothing. 

If you’re looking for ideas, why not try high heels, a garter belt, and suspenders?  Or maybe a sexy costume, like a schoolgirl outfit?  Whatever you choose, it should be something that makes you feel comfortable, sexy, and feminine. 

You can then start to fantasize to help you get even more into the mood.  Maybe you’re a naughty schoolgirl who needs to be punished by her teacher, or maybe you’re a maid cleaning your mistress’ house.  If you’ll be with a partner, they can also help you get into the right mindset.

The Prostate

Along with your mental state, this is the key to unlocking that fabled sissygasm. 

If you don’t know, the prostate is an organ located in a man’s groin.  What it does in the body isn’t too important for us, except for one thing – it allows men to experience great pleasure from anal penetration. 

If you’ve heard people talk about the p-spot, this is what they mean. 

The prostate is in a slightly different position for everyone, so it might take a bit of experimentation to find it.  You can practice a bit with your fingers before trying for the full sissygasm, but once you find where it is, you’ll know it. 

When you’ve found it you’ll be stimulating it with your chosen toy or partner as your means of reaching sissygasm. 

Everyone’s different when it comes to the pace, force, and rhythm that gets them off, so try until you find something that works for you.


This is optional – it’s perfectly possible to have a great sissygasm without it – but it’s a common part of being a sissy that many sissies enjoy. 

Wearing a chastity cage will stop you from being able to touch yourself or get an erection, which for many people heightens the feeling of being a girl. 

If your cock is locked away in chastity, it can often be called a clitty, which again reinforces the idea that you’re a girl.  But that’s not all. 

Some sissies will wear chastity cages for weeks or even months at a time, and being unable to masturbate for all that time will make you very horny, which might make finding that sissygasm a bit easier. 

Sissies also frequently report that remaining sexually unfulfilled like this for an extended period is very erotic in its own right.

Final Thoughts

Now that you’ve read this guide, you should be fully clued up on sissies, sissygasms, and how to have them. 

We’ll repeat that it’s not always easy to have a true sissygasm, but the journey is worth it and is even very enjoyable by itself.  So, if you’re curious about sissygasms, try to have one! 

It will rock your world like you wouldn’t believe and open you up to all kinds of new sexual experiences. 

Good luck!