The Elite Sissygasm Guide: How to Cum Hands-Free in 8 Steps!

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As her battered asshole slams onto the cock below, her face contorts, and jets of perverse fluid fly out of her cunt. ‘’Fuck, I wish that was me!’’ You think to yourself. You all know the feeling.

But you don’t wish it was your cock sliding into the bowels of a sexually-liberated harlot; you wish it was your hole being defiled so hard that you squirt love juice across the room.

For over a decade, I’ve taught sissies the art of the Sissygasm and showed them how to cum hands-free like a whore. In this guide, I will squirt my secrets in your face.

Whether you’re an aspiring sissy whore, a Gooner looking to diversify his orgasms, or a Femdom Bitch looking to humiliate your sissy sluts further, this is the guide for you.

Not sure which one you are? Take one of my infamous kink tests here to find out where you lie on the Gooner/sissy spectrum. Ready? Ok, let’s begin!

What Are Sissygasms? Meet The Infamous Sissy Anal Orgasm

Sissies might not have been blessed with a cunt in the conventional sense, but they have been gifted with an asspussy that comes complete with its own G-spot; the prostate gland.

Through the correct training and instructions, which you’ll be getting in this guide, the correct stimulation of the prostate can result in a hands-free orgasm that will change your life.

A prostate orgasm is unlike any other, and many sissies will attest that it’s dramatically more intense than jerking their fuck meat and allows them to cum repeatedly and keep edging.

Patience is the key to the Sissygasm, and it’s rarely achieved overnight, but the reward is more than worth it and will revolutionize your Porn-fuelled lifestyle.

So, How to Have a Sissygasm?

My years of experience in the world of Sissification have taught me everything there is to know about the Sissygasm, and I’m now going to show you my secret methods to cum hands-free.

But before we begin, a side note: This guide is intended for sissies with basic anal experience and who can take a dildo in their fuck hole. It’s not the place for nervous anal newbies.

The First Rule of This Sissygasm Trainer is to Keep Those Balls Full!

One of the critical foundations of any Sissygasm is keeping your useless balls full. There are few better ways to cum hands-free than when your dick is aching for attention.

One week or two weeks, the longer, the better. I want that sissy sack tight, aching, and squealing for release before you begin the next steps of this guide. 

Ideally, use a sissy chastity cage to stay disciplined. By all means, feel free to wreck your hole and watch porn while you build up spunk; it’s the perfect way to prepare.

Find The Right Space and Dedicate Time to Your Sissy Prostate Orgasm Journey 

A Sissygasm isn’t to be rushed; you must find the right space to make it happen. Wondering what the right space to cum hands-free is? Here are some key features it should have.

• Somewhere you won’t be disturbed – The prospect of people bursting in one while dressed like a whore with a dildo up your asspussy can cause unwanted stress, so ensure any Sissygasm location is private and all yours. 
• Ample space to experiment with Sissygasm positions – There are many positions to Sissygasm, and I’ll cover them shortly, so you should have space to try them all out.
• Reliable internet and porn-viewing devices – You don’t want your sissy hypno porn cutting out at the critical moment, and you should have ample screens to watch it on.

I often suggest my sissy sluts book a hotel room or an Airbnb to achieve all of the above, as they often provide better Sissygasm positions than their own home.

Light candles, set the lighting to fit the mood, stretch beforehand, do yoga, etc. Do whatever you need to make yourself comfortable; it’ll all serve towards your end goal.

Dress Like a Whore & Keep Your Hand of Your Sissy Clitty

If you want to cum like a whore, you need to look like one. A Sissygasm is a significant milestone in any sissification journey, so always ensure you’ve dressed the part.

Grab your pleaser heels, wrap your perverse body in fishnets and other lingerie, and apply your makeup. When you’re looking as fine as the whores in your favorite porn, it’s time to begin.

If you’re an ill-disciplined sissy whore and can’t keep her hands off her clitty, then don a chastity cage to deter your lust. Its role is reserved for the climactic finale!

Choose Your Dildos Wisely!

Every sissy’s asspussy is different, as are the dildos sliding inside of them. Do your research and find a dildo that’s best suited to your tastes.

Obsessed with black men? Get a BBC dildo. Adore a stiff cock ruining your prostate? Get a hard dildo. Perhaps you prefer a flexible fucking experience, in which case, get a bendable sex toy.

Your chosen dildo should look good enough to make your BJ lips salivate, feel pleasurable, and be a size you can take for hours on end, don’t under or overestimate your anal abilities!

You don’t have to resign yourself to one dildo, either. Why not position yourself between two and suck a cock while working your way to a Sissygasm with the one inside your hole?

Don’t neglect your lube, either. Try to find one that is ideal for prolonged anal use, as constantly reapplying inferior lube that dries out too fast is an absolute mood-killer.

Of course, always use a reputable dildo store to equip yourself, too. Stores like The Dildo Hub have everything you need to kick-start your sissy dildo adventure! Oh, and you also get a hefty discount when you use the code CATHERINEDUFFY at checkout!

Experiment With Different Positions During Your Sissygasm Training 

One of the things that keeps me obsessed about Sissygasms is the diversity associated with them. Over the years, I’ve made Sissygasms happen in various ways. 

I’ve seen my subs cum in their mouths via a self-facial with their legs behind their head as I plunge a dildo into their hole, and others cum from a fucking machine ravaging their ass.

But what are the most effective positions, Mommy Catherine? I hear you ask. Let me introduce you to four of my tried and tested Sissygasm positions that never fail.

1. Laying on your side with your knees in your chest – This position works best on a large bed. Get comfortable, fix your eyes on smut, lay on your side, and lift your legs up towards your chest. Reach behind you, and slide your dildo in and out of your hole. Take your time, and pick up speed. This is an ideal way to hit your prostate and can get intense with a fast tempo.
2. Reverse Cowgirl With a Suction Cup Dildo Affixed to the Floor – Sliding yourself down on a dildo in reverse cowgirl and riding while you watch porn is another ideal position. I suggest raising the dildo to a level that’s comfortable and reducing the strain on your knees. Pound your hips on your rubber friend, and feel the pressure build.
3. The Doggystyle Sissygasm Position – This trusted sex position has played a role in countless Sissygasms. Bend over with your ass in the air and pound your butt from behind, either with your hand or a dildo affixed to a sex machine. This is a relaxing pose of submission that flawlessly lets you watch porn and suck another dildo while you train.
4. Riding a Dildo on a Chair – This is a great way to practice a cowgirl Sissygasm. Sit backward on a chair so that your chest is facing the backrest, and slap a dildo to the seat. Holding onto the backrest for support, slam your asspussy back on that cock like you’re riding a hung Alpha male!

While these positions have all yielded great results during my Sissygasm training sessions, take your time and experiment until you find a position that feels great for you. 

Watch Sissygasm Hypno Porn

A critical ingredient of any Sissygasm training guide is an overwhelming amount of sissy hypno porn melting your brain as you ride cock like the whores on your screen.

Thankfully, there’s a wealth of free and premium mind-melting sissification porn out there to take advantage of, and here are some of my favorite videos that are primed for a Sissygasm guide!

• The Sissymaker II – One of my all-time favorite sissy hypno PMVs. It has a gorgeous build-up, a selection of intense beat drops ideal for upping the tempo of your thrusts, and a slower come-down to ride out the aftermath of a Sissygasm. You can check it out here. Any of EmperorHypnos’ sissy PMVs are pure gold, in my opinion.
• Work, Bitch! – A Sissygasm requires you to work for it, so this sissy hypno PMV featuring the Britney Spears track, ‘’Work, Bitch!’’ is ideal. There’s tonnes of reverse cowgirl shemale action in this video, too, so it’s perfect if you’re chasing a Sissygasm through that position. Give it a watch here.
• Hung Up – This iconic Madonna track is gorgeously suited to Sisssygasm with the perfect beat to match your dildo riding tempo. The beat is great for working your way into it slowly before upgrading to a relentless assault on your prostate. Give it a try here.

To fully immerse yourself in the porn, I suggest using noise-canceling headphones and amping up the volume (to a safe level) to truly melt your feminized mind.

Also, don’t miss my popular guide on some tried and tested tricks to make sissy hypno porn more effective.

The Humble Mirror: Unsung Hero of a Hands-Free Prostate Orgasm?

‘’Look at you, you nasty fuckin’ whore!’’ These are the kinds of thoughts that should be crawling through your porn-crazed mind as you pursue the elusive Sissygasm. 

This is why, along with some high-grade sissification hypno porn, I advise all aspiring sissies to use a full-length mirror in their Sissygasm journey to observe their debauched reflection.

The use of a mirror can have a tremendous effect on achieving the sissy mindset, especially when used base for a suction cup dildo or beside you as you wreck your hole.

Become the living image and embodiment of porn. After all, there are few things hotter than the very sight of your slutty body being the root cause of your eventual Sissygasm, right?

Wait… What’s Happening?

Picture the scene; you’ve experimented for hours on end and are now going cross-eyed in the grip of anal pleasure. Your mind is melting after endless loops of sissy porn and PMVs.

Your shaking body is fuelled by pure, feminized lust and is begging for release, but your caged sissy clitty denies it, causing it to seek an eruption through alternative methods. 

As you hammer your prostate in a position that feels divine, you begin to feel an odd feeling inside of you. It’s almost as though you’re going to piss yourself. 

Do not fuckin’ stop, you whore. That’s an order! Initially, your first Sissygasm can feel overwhelming and daunting, as it’s something your body has never pulled off before.

When you feel it coming, drive it home and focus every ounce of porn-fuelled lust you have left. Hammer your hole, drench your mind in porn, deepthroat a rubber cock, do whatever it takes.

Some sissies have reported feeling like they’d pass out from the intensity of the orgasm, only stopped by the wet sensation of cum pouring involuntarily from their caged sissy clit.

Congratulations; You’ve Cum Hands-Free! Your Life Has Now Changed Forever

A Sissygasm is classed amongst the more elite tiers of my notorious Sissy Slut Test and for good reason. 

Cumming hands-free via a prostate orgasm is something that only the most dedicated of sissy whores can achieve. The mere fact that you aspire towards one makes my cunt flutter.

After a hands-free Sissygasm, it’ll change your life. You can now ride Alpha men’s cock and squirt like a woman and even watch porn, experience multiple orgasms, and keep going.

My darlings, I wish you the most perverse of luck in your journey and hope this elite Sissygasm guide has given you the knowledge needed to achieve your hands-free orgasm dreams.

If you’re a Sissygasm veteran with some additional tips to share or wish to know some specific tips to help you in your journey, drop a comment below. I can’t wait to hear from you!

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