Sissygasam

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Sissygasam
Shane is our lovely LGBTQ writer from San Francisco. He loves tapas, red wines and hiking Bay Area trails with his husband Jake.
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In this guide on how to sissygasm, we’ll teach you everything you need to know to become a sissygasm master.
Achieving the elusive sissygasm is not only possible. It’s a great way to achieve a better, more satisfying sex life. We will go through the process of attaining a hands-free sissygasm, including the benefits of doing so, how to prepare for a sissygasm, the process of achieving one, and the resources available to help you get there.
But let’s first define what a sissygasm is, so we are on the same page
A sissygasm is a hands-free orgasm, meaning no penis stimulation is involved. Instead, you achieve ejaculation by stimulating other erogenous zones like the prostate gland, nipples, perineum, or even through mental stimulation. During the sissygasm session, the penis can be hard, flaccid, or trapped inside a chastity cage.
A sissygasm can be achieved with a partner or alone, and you can use dildos, vibrators, fingers, or even your partner’s penis.
Keep in mind is that a sissygasm requires much more patience than a regular orgasm. It will take time to get in the right mindset and learn how to do it properly.
The benefits of achieving a true sissygasm are many, but some of the most common ones are:
From my own experience, a hands-free prostate orgasm feels better than a regular orgasm. It’s difficult to describe, but the buildup feels like a peeing sensation combined with a slight pressure behind the penis. When the anal orgasm occurs, I feel it more in the pelvic areas than in my penis, a feeling new to most men. Some men also experience leg spasms, but I have not had that yet.
In addition, it feels like you are in a blissful state of self-love. It’s the state of feeling happy, comfortable, and secure in yourself.
Finally, the cum can either slowly leak out (oozing) or strongly shoot out across your entire body. It can be just a few drops or a full load. Many sissies also like to shoot the load in their mouths.
LatexLucia_ from Reddit explains it like this:
It’s a really continuous and warm feeling for me. At first, it starts to feel like a need to pee, then it slowly fades into pleasure. After that, it gets super intense right up to orgasm. Mine leave me shaky and out of breath, they seem to get more intense each time (I’ve recently gained the ability to orgasm from anal only.)
Below are the 5 steps that worked for me. However, all bodies are different, and you may have to adapt these steps to suit your unique needs.
It’s recommended that you refrain from masturbation for at least one week before attempting an anus orgasm. This no-masturbation period will help build up sexual pressure and make you hornier.
Pro Tip: A cock cage will help during this phase.
You must be in the right mindset for the sissygasm journey.
You need to be relaxed and present in the moment. Don’t overthink it.
A sissygasm is a long process that requires much patience and time, and if you have an open mind, it will be easier to achieve the boy pussy orgasm.
In addition, it’s important not to stress about the orgasm. Let it occur when it does, and learn to enjoy the journey instead.
Pro Tip: It may help to dim the lights and put on some seductive music.
Dressing is a personal choice, but most sissies like to dress up for their sissygasm sessions. It can be a sexy outfit or just some sexy lingerie.
I recommend wearing something that will be comfortable during the sissygasm session, like a comfortable pair of underwear and a comfortable top.
Also, make sure you have a clean body. Take a shower and wash your hands. If you don’t have access to a shower, you can clean the genital area with a baby wipe. You can read more about anal sex prep here.
Pro Tip: To heighten your senses with sensory deprivation, try wearing a blindfold.
P-spot stimulation is the most straightforward way to achieve your first sissygasm. You can use dildos, vibrators, fingers, or your partner’s penis.
If you’re a beginner, I recommend a prostate massager, like Lovense Edge 2 or Lelo Hugo. These sex toys are designed to hit the sweet spot directly, making it easier to focus on the right mindset.
Pro Tip: The best sissygasm position is missionary style, but I suggest trying different positions as well (All the best positions for anal masturbation are here). You can try doggy, spooning, cowgirl riding with suction cup dildo, or on your stomach (prone), and please use plenty of water-based lube.
Born2beasissy from Reddit gives this excellent tip:
YOU DONT REALLY NEED TO PUSH YOUR DILDO IN AND OUT LIKE A MANIAC to reach a sissygasm. Push your dildo in, lay on your back, cross your legs, and use your ass muscles (Kegels) to squeeze the dildo. Like you are trying to hold your pee. Squeeze and relax. Do it slowly. Be patient. Use lots of lube.
For more on anal play and P-spot orgasms, I can recommend our extensive guide about prostate milking.
It takes a lot of patience and practice to master the sissygasm game.
Confession: I have only achieved it a few times, and I have practiced for over a year.
If you haven’t achieved it yet, don’t worry. It takes time to learn, and you will be able to achieve it in time.
How long does it take to sissygasm? Well, there is no concrete answer to this question because we are all different. In my case, it took one month of rigorous training, but I have a few friends that achieved it quicker.
For best results, I recommend practicing every day. Try it for at least 30 minutes and try to relax while doing it.
Repeat, repeat, then repeat some more.
Here are a few external resources to help you on your journey:
My journey into sissygasm has been an amazing one, and I’ve never experienced anything like it.
The best part of the sissygasm is cumming. I love how the semen feels. It feels like an orgasm but also like a warm hug.
It feels great to know that you can achieve this, and that it’s possible with some training and patience.
To me, sissygasm is an amazing, amazing experience, and I hope my sissygasm guide has motivated you to try it too.
Thanks for reading my hands-free prostate orgasm guide!
PS, check out this guide for more anal masturbation tips .

Are you ready to go “ Down The Sissification Rabbit Hole?” Then read this…
H ave 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!
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).
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.
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.
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!
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.
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 .
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.
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.
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.
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!
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!
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…
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.
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
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