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A Guide To The Elusive Sissygasm

guide to sissgasm

Have you ever watched one of those videos where the cute-as-can-be sissy is sitting back on her calves, riding a dildo for all she’s worth, when all of a sudden her limp—and possibly even caged—clitty begins to leak a little cum while she experiences one of those earth-moving sissygasms? Her post-orgasmic spasms appear to reverberate throughout her entire body?

I don’t know about you, but I become extremely envious while watching her achieve something that I’ve always considered an unlikely, if not near-impossible dream. These frustrating fantasies about having that elusive sissygasm is about to change for me—hopefully sooner, rather than later. I’ve decided I’m ready to have one!

The Definition of a Sissygasm

Before we travel too much further down this feminine-like orgasm path, let’s define what exactly a sissygasm is. Over the past year or so I have, more-or-less, moved past masturbating like a male in exchange for cumming in a more lady-like manner.

With my limp clitty tightly tucked downwards into the open-ended liner of my panties—like it is situated 98% of the time anyway—I gently rub (or ‘nub’ if you will) the underside tip of my panty-encased clit with one, meticulously manicured finger.

Although this is an exquisitely feminine way to cum—much more erotic than just jacking it—it’s certainly NOT a sissygasm (as we’re defining it here anyway).

ready for her first sissygasm

Most would define a true sissygasm as a hands free type of orgasm (aka HFO). The tricky part, is that there are different ways for a sissy to achieve a HFO. Nipple play is one way. Anal or perineal stimulation, without involving the prostate gland, is another.

By harnessing the sexual power of your kinky little mind, I’m sure it’s possible to experience a HFO in several different ways. Many GG’s have reported having a much-coveted whole-body orgasm simply by having their toes sucked on. No reason a sissy such as yourself couldn’t have that happen.

For the purposes of this article however, let’s focus on the more common type of sissygasm: one that is is achieved from anal (sissy pussy) penetration only—typically involving stimulation of the prostate gland/P-spot with a finger, prostate massager, dildo or maybe even a real, live cock.

Below is a conceptual introduction into the anatomy of a prostate orgasm—or sissygasm.

prostate orgasm

If you’re perhaps looking for a prostate stimulator that will help pull this off, you might find this article on prostate massagers interesting.

Many, if not most, sissies report that achieving a sissygasm is not so easily accomplished and… I can certainly confirm that. Still, with practice, we sissies have more than ample video proof that it can be done.

The consensus of sissies (and others) who experience these types of sissygasms on a regular basis is that once you have mastered getting off this way, the typical ‘manly’ methods of release are immediately moved into the ‘highly inferior’ category.

A Sissygasm Disclaimer

As I write this, I’ve yet to experience my first real sissygasm so… what exactly qualifies me to write on the subject? In the truest sense, I’m not qualified one fucking bit at all. But, I have read and studied-up on sissygasms quite a bit. If you’re reading this, maybe you have too.

But more importantly, I’ve made a commitment to having my first girly-girl O, sometime in the not-to-far-off-future. In any case, by the time you wind reading this article, hopefully I will have been lucky enough to have had my very first sissygasm.

To that pleasurable end, I’ve purchased a Nexus Revo 2 rotating prostate massager. In addition, I’ve made a vow to myself to remain limp—with the help of limp clitty training hypno—and chaste until I finally do have that first, elusive sissygasm. Keep those pretty little fingers crossed for me sweetie!

Relocating Your Erogenous Zone

relocate erogenous zone

The idea behind achieving a sissygasm is to psychologically move your erogenous zone back, from the base of your sissy clitty, across the perineum, to your sissy pussy. It’s imperative to STOP thinking of your smallish—and hopefully shrinking—sissy clitty as your primary, or even secondary sexual organ.

Are you a man or a sissy? Sissies don’t jerk their clitty’s so it’s time to come to terms with who you really are. How are you ever going to be able to cum like a girl if you continue to think and act like a man? I realize that this major shift in sexual conditioning—from male to female—is not necessarily for every sissy. It certainly wasn’t for me until until I was further along in the sissification process.

If you’re not willing to give up jacking off and fucking girls, then that’s perfectly okay. All it means is that you’re not yet ready to fully embrace your femininity and learn to cum like a lady.

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Once you begin to mentally relocate your primary sex zone to your pussified ass, it’s time to support and enhance that feeling with something physical. That means sticking your favorite toy up your sissy pussy while refraining from touching that, preferably limp and hopefully caged, sissy clitty.

If you wanna know more about anal toys, like dildos, then you might want to read this Sissy Dildo Guide.

A Psychological Sissygasm Stumbling Block

sissygasm stumbling block

Achieving a sissygasm is all about relaxing and letting things happen. Let’s be honest—most biologically-born males have spent the majority of their lives perceiving their assholes as anything but an erotic erogenous zone.

Both men and women have been socially conditioned to regard their poop-chutes as just that: a dirty, disgusting hole that nothing should ever be allowed to penetrate—no, not even a thermometer. Obviously, that narrative needs to change in order to fully express your rearward sexuality.

The truth of the matter is, who is anyone to authoritatively say what any hole on our body should be used for—or not? Sure, it typically hurts a little (or a lot) to have something inserted into your sissy pussy for the very first time.

The beauty of the human body is that it’s incredibly adaptable. To experience an anal orgasm, one must adapt their thinking to where your sissy pussy becomes a source of erotic pleasure. And with some time, along with proper training, it certainly can become exactly that.

Setting Up The Sissygasm Scenario

sissygasm scenario

Since we both know that our brains are the most powerful sexual organ, it makes sense that a sissygasm should begin in your pretty little head. Attempting to attack your P-spot with a dildo, trying to force an orgasm, rarely works. Starting things off with a sexy scenario is the preferred way.

I like to get all dolled up: full make-up, bra, panties, nylons and heels. I keep my clitty caged. Then I begin to visualize my most favorite erotic fantasy through my mind. You may prefer to watch a video. Only after I’m physically, psychologically and sexily set-up do I insert the Revo 2 into my pussy.

We definitely knows the professional of prostate orgasm between movie stars. The name of her Christina Hendricks, she has some leaks on her phone, with some massage things.

It typically takes a genetic girl some time to get warmed up… and then even more time to eventually orgasm. It’s the same with us sissies. Enjoy the pleasure you’re allowing your sissy pussy to experience without harboring expectations that you need to cum. Let your sexual fantasies run wild and see what transpires.

Achieving a sissygasm can be a challenging climb, especially while wearing heels. The first one may take awhile. However long it does take, my admittedly novice advice would be to just relax and thoroughly embrace, and enjoy the process. That’s how I’ve decided to approach my sissygasm quest.

The Three P’s To Achieving a Sissygasm

sissygasm three p
  • Practice
  • Patience
  • P-spot

Achieving a sissygasm on your first try is not the normal experience. For most sissies, and even real men, it takes a good amount of practice. That’s the first “P”, practice. Sissygasms should be treated just like any skill you would endeavor to master. It will take committed, consistent practice over a period of time to get good at having them.

As I alluded to in the previous section, some patience will also be required. Move on from the narrow-minded, unfulfilling male mindset of getting sexual relief as quickly as possible. As a sissy, you want to bask in patient, pleasurable, erotic excitement. Let your sissygasm happen—rather than trying to make it happen.

The third “P” to achieving a sissygasm is the P-spot that you will want to stimulate. Stick a finger up your pussy a couple of inches and you will feel a smallish, oval-shaped ball that is located towards the front (anterior) of the body. That’s your prostate gland. Every sissy’s P-spot will be in a slightly different place. With patient practice, you will eventually find where that seriously-significant spot is.


What you use to stimulate your P-spot is a decidedly very personal matter. It could be a prostate massager—there are so many to choose from—or some sort of regular dildo. Some sissy’s have luck using just their finger. If you’re into men, maybe you can find a boyfriend who can hit your P-spot with a perfectly placed movement or motion.

The consensus of sissies who have experienced sissygasms on a regular basis, is that after the first one, the second is much easier to cum by. That is very encouraging to hear!

Sissy Training

Chastity and Sissygasm – The Dynamic Duo

chastity and sissygasm

If you’re the hopelessly impatient type, staying chaste for an extended period of time can speed up the sissygasm process.

Depending on your age, that ‘extended’ period will vary. One week may seem like an eternity if you’re younger. An older sissy like me—who also listens to a lot of limp clitty training hypno—won’t bat a fake eyelash at a month.

As many sissies will arduously attest to, remaining in chaste mode—preferably with the help of a chastity device for a prolonged period of time can create an undercurrent of unfulfilled desire that can be highly erotic in its own right.

Some would argue that this is the preferred state that any sissy worth her lingerie should be constantly striving for.

And when that elusive, mind-shattering sissygasm does eventually materialize, I’m fairly certain all that waiting will be worth it… and then some!

Sissygasm Update – July 2020

Since originally writing this article I’ve gained more understanding involving the process of achieving a sissygasm. If sissification is a process, then having a sissygasm should serve to re-emphasize that same word… process.

After years of perfecting the art of cumming like a man, I can personally attest that rewiring your brain and retraining your body to orgasm in a more feminine-like manner can be a daunting task.

When it comes to sissygasms, I’ve come to three conclusions…

  1. You gotta be completely committed and dedicated to having one.
  2. Although in theory it sounds like a good idea, staying completely chaste until it happens doesn’t always work so well in real life.
  3. It might be wise to find a ‘bridge’ type of orgasm—something between nubbing your clit in your panties and a full-on legitimate sissygasm.

I talk a lot about practice earlier in this article. That means a metric ton of consistent and dedicated practice!

Remaining totally chaste for a lengthy (more than a month) period of time—for me anyway—turns up the sissy-sex-barometer to levels where it’s difficult to think about anything other than sissification.

Finding yourself in a never-ending erotically aroused state sounds nice (and it is), but it can seriously interfere with one’s ability to concentrate on the non-sissy parts of your life.

I recently found myself in that predicament—after three weeks of remaining chaste—I was too horny to think. I didn’t want to completely destroy the sissy erotic zone I was experiencing with an orgasm, but I felt the need to take at least a little of the edge off. But how?

While getting ready to practice yoga at home one day, I decided to lay down on my yoga mat in a plow position (on my back, legs positioned horizontally over my head) while naked. Just for fun, I wanted to see how close I could get the tip of my sissy clit to my mouth.

Since I was so incredibly horny, I couldn’t resist the temptation to reach up and very lightly diddle the very tip of my clitty between my thumb and forefinger. Partly because my nails happened to be long and painted that day, the sensation was incredible. Just an light flick my nail on the very tip of my clitty proved to be overwhelming.

Sissy Webcam
sissy swallows her cum

I felt a modified orgasmic-like contraction and after 5 seconds or so, a small amount of semen began to drip out of my sissy-clitty, directly into my mouth. The scene was similar to the one above (except that it wasn’t a steady stream—and I’m not a blonde).

This continued about 6 more times in succession within the span of 30 to 40 seconds. It felt something like an drawn-out variety of a ruined orgasm—except strangely satisfying in its own, unique way.

Afterwards, although the sexual edge had subsided somewhat, I hadn’t lost all of my sissy mojo, only a small segment of it—which enabled me to now focus on other important aspects of my life.

The interesting thing is that after this protracted orgasmic experience, I definitely did NOT feel that I had, in any way, shape or form, just cum like a man. It felt deliciously all girly-girl.

Have I inadvertently stumbled upon some missing sissy psychological link that will serve as a bridge to eventually experiencing that elusive sissygasm? It’s way too early to tell… but I’ll keep you posted.

In Search of the Perfect Chastity Device?

If you think that a chastity device might help in keeping you chaste for and extended period of time (how could it not?), then you might want to check out my Sissy Chastity Devices page.

On it, I answer some common questions and there’s a lot of useful information about different types and styles of chastity cages that are available.

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