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

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.

”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.”

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.

Discreet chastity cages for day-to-day public sissy life

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 

Having a soundgasm through overheard sex at a Russian hotel.

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.

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. 

A cheap fucking machine is great sissy training equipment

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. 

Cock sucking hypno for sissies

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!

16 COMMENTS

  1. Getting into the mindset is the biggest challenge. Being horny is not enough, I need to feel like a total sissy whore. Having an hour long audio hypno as a starter was the key. Ill never forget the leg-quaking feeling as I dribbled my load from my limp clitty onto my chest.

    Lovely read!

  2. I had my first sissygasm recently, naked on the tile in front of my fireplace, all holes filled up so well. It was amazing. Silicone is amazing. When it started to pour out I felt like a real woman for the first time in my life. It was delightful. I can’t wait to do it again, next time in heels…

  3. I like the all clear plastic ones with a thick platform that are really high, but I also really can’t get enough of gold gladiator type sandals that wrap up the legs and have a stiletto heel. I used to lust so hard over women in heels like that, then I realized I could be a woman in heels like that…the clear plastic one show off the feet so well and make them sweat a bit. I love seeing painted toe nails on the clear plastic. There’s this sense of sluttiness and elegance all at the same time

  4. I like the all clear plastic ones with a thick platform that are really high, but I also really can’t get enough of gold gladiator type sandals that wrap up the legs and have a stiletto heel. I used to lust so hard over women in heels like that, then I realized I could be a woman in heels like that…the clear plastic one show off the feet so well and make them sweat a bit. I love seeing painted toe nails on the clear plastic. There’s this sense of sluttiness and elegance all at the same time…

  5. I had my first prostate orgasm when I was 19. It was late at night and I was waiting to hear back from a prospective hookup. I couldn’t wait any longer, so I gave up on him and stripped completely naked, put down a towel in front of my TV and generously lubed my body up with coconut oil.

    As soon as I got my favorite PMVs playing I lay down on my side amd started touching myself with my fingers, just gently probing myself until I felt loose enough for my glass toy. I was all warmed up pretty quickly and it wasn’t long before I had built up a breakneck pace, moaning like a whore and clenching my hole on the dildo all the while. When I started to cum, my body became red-hot and then my brain just completely shut off. It felt as though I was getting rocked by wave after wave of pure bliss. I passed out and woke up a couple of hours later, drenched in sweat and all the good stuff.

    All I could think to do was go back for round two! I made myself cum 8 more times and by then I was too exhausted to keep going. In total I punished my hole for more than 6 hours and I’d say that night absolutely changed my life in the best way. Anal is simply the best!

    • Incredible! It’s stories like this that I love as they inspire so many others to chase the Sissygasm achievement. That sounds like a divine session I would have loved to have been a fly on the wall for. Thank you so much for sharing! x

      • Of course! Your content has been such a great inspiration for me for the last 2 years, so I feel like sharing my experiences is the least I could do!

  6. This is truly a great article. My first sissy gasm came after an almost 2 day binge, with like 5 hour sleep and straight back to gooning. Starting my gooning session with a pair of dirty panties I found left outside at a dogging site and countless hours of edging led me to ordering a next day delivery bbc thrusting dildo. Gooned the whole night and even pissed all over myself and let it dry on me while I gooned to pervert heaven. Eventually when the dildo arrived. I got my monitors hooked up to all the porn I loved and just fucked my ass for 30 minutes, all the edging had me on the edge and the bbc in my ass finally had me erupt, my cock had been edged so long it came limp. Felt incredible.

    • That sounds divine! I especially love the crusty panties from the Dogging site, I always love it when I find some sleazy relic to add to my Goon Fuel collection. The image of your limp dick spurting from a BBC dildo is making me drip between the thighs x

      • curently on a 8 hour binge, got an escort coming tonight. Paying just to suck and lick her ass and feet. and she’s bringing a few used condoms from other clients for me to use. gnna be a great night

  7. Both of you ladies sound like real anal whores—how delightful 😉

    I’ve also put a dildo on one of those large exercise balls and bounced up and down on it in front of a mirror until I came, while also deepthroating another dildo. Watching my tiny dick bouncing up and down in the mirror made me feel like a true sissy whore. The exercise ball is so great for solo sex because you can bounce so hard. The first time I did it was a gay fantasy, which helped me come to terms with my bisexuality. It was summer and I was sweating profusely. I knew for sure I was bisexual after that experience. I’ve jerked off many times thinking about that night. The second time I had on high heels and a fishnet bodysuit. Both times I slurped my own cum up, on all fours, off the floor. I immediate told one of my girlfriends about everything I did.

    • Oh, what?! I have an exercise ball at home and it never appealed to me to use it for riding my dildo. Love this idea, I’m going to try it out tonight and will be assigning it to my sissy subs, too! Thanks for sharing, Davina. Also, the image of you spurting and slurping while wearing a fishnet body suit and heels is making my slit throb! x

  8. If it’s not possible to get it without long abstinence, I’ll never get it.
    Because for me, abstinence is absolutely not possible. Even for one day.

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