How to Sissygasm: Your Guide to Hands-Free Prostate Orgasms

Maybe you've heard about sissygasms and are wondering what all the hype is about. Or perhaps you are just curious about sissygasm training, and want to see if it is right for you?

You're in the right place! Welcome to Kinkly’s Sissygasm Guide, where you will learn everything you ever wanted to know about how to sissygasm. We'll take you step-by-step on your journey toward anal orgasmic bliss (for real!).

What is a sissygasm?

Let's start with the absolute basics. Urban Dictionary says a sissygasm is a “hands-free orgasm” (HFO) usually obtained “exclusively through anal stimulation.”

Sex columnist, Zachary Zane, author of ‘Boyslut: A Memoir and Manifesto,' defines a sissygasm as “when a sissy (often, a crossdressing man who likes to be feminized during sex) orgasms through anal stimulation without touching himself.” 

Specifically, without touching his penis. Okay... so, how exactly does that work?

Often, this form of prostate play is achieved via partnered sex by “being pegged, fisted, or another form of anal stimulation,” says Zane. Sometimes, it may be accompanied by consensual degradation, demeaning or humiliating insults of a sexual nature.

“The sissy may refer to his anus as a ‘pussy’ or ‘sissyhole’ during sex and may like being called a ‘little bitch’ or something of that ilk,” says Zane.

In addition, a sissygasm may also be a part of forced feminization (sissification), or sissy training, which “refers generally to the feminization of a person who identifies as male.” Sissification is often linked with s/m sex and humiliation play “among heterosexual, cisgender men,” in which the man may also participate in slut training.

Read More: I Feel Pretty: A Guide to Sissy Play

What does a sissygasm feel like?

“Orgasms are like grains of sand; no two are exactly alike.” Annie Sprinkle

I love that quote from Annie Sprinkle, because it reminds us that every body is different and how we experience pleasure and orgasm is also unique.

While some people will find sissygasms easy to achieve, others may find it more elusive. If you're trying to have your first sissygasm, it may require rewiring your body and brain to experience a different type of pleasure.

Keep in mind, orgasm doesn’t have to be the goal of sexual exploration and it isn't the only way to have a good time. Simply enjoying the pleasure and exploration of something new can be just as exciting.

Since we are talking about orgasms, let’s get into the dynamics of how a sissygasm happens.

Penis owners have a prostate (aka p-spot or male g-spot) which is a highly sensitive organ surrounded by nerve endings. It is responsible for producing and ejaculating prostatic fluid. This organ is located on the anterior wall of the rectum, and when stimulated, can play a significant role in contributing to sexual pleasure and anal orgasm in men.

Author and editor, Jon Pressick writes about milking his prostate during a hands-free anal orgasm experience that he describes as an “explosion”.

“Like some other people with penises, mine is usually flaccid when I receive anal stimulation. But then, it twitched, and twitched some more… the rush of impending orgasm was now undeniable. It rolled throughout my body, overtaking every muscle and inch of skin. It started in my ass, radiated out, and then zeroed in on my penis… And then it happened. The explosion. The intensity. The complete, full-body release.”

Other folks have described sissygasms as an “undulating," “radiating pleasure,” with “numerous peaks and valleys in terms of arousal and excitement,” ending in “full body shakes and convulsions," or even multiple orgasms. 

Since this type of orgasm is hands-free, which means there is no penis stimulation involved, you may or may not experience wet ejaculation, though this is often shown in sissygasm porn.

How long does it take to sissygasm?

Pleasure (and orgasm) are all about personal preference, and the way we are erotically wired. Therefore, time to orgasm may vary “anywhere from 30 seconds to a couple of hours!” notes Zane. He adds a reminder not to rush, for the pleasure is in the journey itself.

How to Sissygasm

Use the following step-by-step instructions for how to sissygasm and as a basic blueprint, then enhance as you see fit.

Step One: Communication

If you are having partnered sex, discuss what to expect during anal sex and establish consent. Open communication is key to having a safe and enjoyable experience. 

Step Two: Relax and let go

One of the biggest obstacles to orgasm is being too much in your head or worrying about your performance.  Do whatever helps you relax and allow yourself to just let go.

Step Three: Hygiene

Most people like to clean up before engaging in any type of sex. A simple shower and wash with mild soap and water will do the trick. If you feel you want a more thorough cleaning, you may want to consider an enema, but it is not necessary. 

Step Four: Gather your supplies

The following are our must-haves for a great anal sex sissygasm experience:

Add an old towel or Liberator Throw to protect your sheets during messy sex. 

Sexual lubricant is essential with anal sex, especially since the anus does not self-lubricate. We like Wicked Jelle Anal Lube and Bijoux Indiscrets Anal Play Gel.

Adding anal toys can help you sissygasm, especially if this is your first time trying anal. We recommend starting with something small, like a butt plug. 

Pressick says a vibrating butt plug is what does it for him.

“The vibrations really are the key. Not too fast or strong at first, I like to ease into the sensation. Each time I increase or change the speed or intensity of the vibes, my penis jumps. I know I’m on my way, but it is a journey.”

The b-Vibe Anal Training Set is a great starter toy for those new to anal play, and it comes with three vibrating plugs of various sizes!

Certified Sex Educator, sex toy industry veteran, and product expert, Casey Murphy suggests the Strap-on-Me Sliding Skin Realistic Dildo, and the Evolved Gyro Vibe, both suction cup toys. 

“Since you can't stroke it out, ride it out! A suction cup dildo will work the prostate to a mind-blowing sissygasm through an effortless, hands-free experience. Stick the suction cup to any flat surface and start slowly while the prostate plumps with every thrust.”

Finally, another great toy design for going solo is a prostate massager like the Aneros Vice 2 or Aneros Helix Syn Trident. Aneros toys are uniquely designed to massage the prostate using the muscles inside your anus, for hands-free anal orgasms.

Step Five: Warm up, go slow & establish boundaries

Sensual touch and getting turned on before any type of penetrative sex with hands, lips, fingers, or toys is a great way to warm up. Take it slow and allow your body to adjust to the stimulation. 

Read More: Sensual Touch: How to Have Mind-Blowing Sex Without Penetration

Step Six: Boundaries

Notice the difference between something feeling good, and something going beyond your comfort zone. Don’t try to force something too big, or too fast, and don’t be afraid to let your partner know if you want to stop.

Step Seven: Positions

There are lots sex positions that are perfect for back-door penetration like Doggie style, Leapfrog, Happy Baby, and the Eiffel Towel Sex Position. Experiment with a few (or all of them!), and decide which position hits exactly the right spot.

Step Eight: Practice

Not going to lie, it may not be great the first time. But like anything, the more you practice the better it becomes. Or you may decide that sissygasms are not for you, and that’s okay too. 

Step Nine: Try Chastity

Some penis owners enjoy playing with chastity — caging the penis and abstaining from sexual pleasure — to heighten orgasm when it does happen.

Step Ten: Get Kinky

Any type of BDSM can be introduced, as long as partners are game and there is consent. Sissy play often has elements of domination and submission dynamics involved, and there's a whole lot of kinky play to explore!

The Bottom Line

Exploring sissy anal play offers new discoveries in pleasure, intimacy, and orgasm. As you begin your how to sissygasm adventure, the key things to remember are to prioritize safety and consent and to have open and honest communication.

Remember: while some people will enjoy these types of orgasms more easily, others may find that it is not their cup of tea. With practice, you can always get better or decide you want to try another type of pleasure instead.

The important thing is you have explored your potential pleasure and learned something new about your body. Congrats! Now go have fun.