The Sissygasm Guide
itsybitsysissyPreparation
What is a Sissygasm? What types are there?
Prostate Stimulation a.k.a. Milking
Deep Anal Stimulation
Learning to cum without cumming
Multiple Orgasms
The Plateau
Extending Erogenous Zones
The ultimate Sissygasm

This Guide will teach you all you need to know about Orgasms, so you can cum like a girl.
Chapter 1: Preparation

To prepare for this guide first you must read my anal-prep guide. Not only will it teach you how to prepare your sissy pussy, but – even more importantly – it will tell you exactly what tools you’ll need. The right dildo is essential if you don’t have a real cock around that you can ride!
Chapter 2: What is a Sissygasm? What types are there?

What is a Sissygasm? Well there are different views about that. Just like the word Sissy means different things to everybody who identifies themselves as one, so does the word Sissygasm mean something different depending on who you’re asking.
Just look at different captions from different authors saying "this is the only way a Sissy is supposed/allowed to cum". They often contradict each other.
I’ll now list some examples ordered by how advanced I think they are:
- Ejaculating from wanking under certain conditions (e.g. only when you cum in your own mouth and swallow, only while in chastity, only while being plugged/having something stimulate your ass, only by wanking your limp clitty with two fingers, only ruined orgasms, …)
- Ejaculating from Prostate Stimulation with manual or technical support (e.g. vibrator, fuck machine, …)
- Hands-Free Ejaculation from Prostate Milking
- Ejaculation from Anal Stimulation (w/o Prostate Stimulation)
- Orgasm from Anal without Ejaculation
I’ll not teach you the first way for 3 reasons. 1) I don’t consider those real Sissygasms. 2) They are pretty self-explanatory. 3) There are way too many different ways.
Chapter 3: Prostate Stimulation a.k.a. Milking

So let’s get to business. I assume at this point you know how to clean your colon, have a perfect curved dildo and you are able to stretch your sphincter so the dildo will fit? Perfect!
Basically all you need to do is put your dildo into your pussy with the tip pointing towards your belly (so it curves to the front not the back), find the prostate and start stimulating it. You may fist want to try finding your prostate with your fingers. Simply describe a circle with your finger palpating the wall of your anal cavity. In the front you’ll find something that feels different – a kind of lump. That’s your prostate! If you feel a lump somewhere else go to a doctor!
Now try to find your prostate with your dildo. It can feel a bit like touching your clitty or like a slightly painful pressure on your urethra. Now all you have to do is stimulate that region of your ass until you cum.
Some good positions for prostate stimulating are:
- Riding a dildo that’s mounted on the (e.g. shower’s) floor.
- Laying on your back with both hands under your ass and the feet in the air, fucking yourself with your dildo or being fucked by your man.
- Being fucked doggy style on all fours.
Results:
Some Sissies only dibble out a few drops of their sissy cummies, others will spurt out loads. You can try to make your orgasms more productive by additional stimulation, e.g. by wanking or by using vibrators or fuck-machines, but keep in mind that smaller loads are actually more natural for most Sissies. If you are on hormones already you may even be unable to ejaculate anything more than a little precum at all – and you’ll love it!
Chapter 4: Deep Anal Stimulation

Now that you had your first Sissygasms let’s try to go a little deeper.
This time the goal is not to simply cum, but to maximize the pleasure.
To do that turn your curved dildo the other way, so it points to your back – away from your prostate. The dildo will go past your prostate without stimulating it and go deeper into your pussy – so make sure you don’t go to fast the first time!
Ride your dildo like that for a while and try to take in all the sensations you get from stimulating your insides.
After a while turn your dildo around 45° (or turn yourself on it) so the tip is now pointing to the side. Do this to stimulate different parts of your colon. Then turn to the other side, ride on, then turn, … and so on.
If you experience waves of pleasure going through your whole body, making you shiver and loose control, then congratulations! You just came like a real girl.
If not, that’s fine. Don’t expect this the first time(s), it will come with time. Instead – if you want to climax – just point your dildo to the front now and continue riding it/fucking yourself. Maybe try not to make it too obvious that you are stimulating your prostate but keep stimulating all of your pussy. That way you’ll teach your body that you can reach extacy from anal stimulation.
Chapter 5: Learning to cum without cumming

If you already had a girly orgasm without ejaculation by following the previous chapter read this one just to learn how to make the experience even more pleasurable. If you didn’t, then the following tips will get you there.
1) Make it tight
In the previous chapter I was talking about pointing your dildo alternately to different sides of your colon-wall. Now let’s try to stimulate all around at once! To do that you have to increase the pressure in your belly. There are two ways to do so. One is to flex your belly muscles like while doing a sit up, the other is to do the same with your pelvic floor muscles – like when you take a dump.
Play around with both, combine them, increase and decrease the pressure periodically, push in and push out at the same time, … basically try different things to get different stimulation and increase the pleasure – oh and his of course! This will feel awesome for him as well.
Pro tip: Before your fucksession do some sit ups or other abs workouts. The perfect point is to stop just before you’d get a muscle cramp. Do that if you want to have the tightest pussy around.
2) Change position, velocities and dildo
I like to start out by riding my dildo in the shower, because it’s a great way to make sure I’m really clean. After a while I move to the bed and try a few positions there. Make sure you change the dildo-curve-direction along with the position. Try different velocities and depths as well. A good idea is to watch a porno while fucking yourself with your dildo and reenacting it.
3) Basically variety increases pleasure
Switch around between rough and gentle, deep-stimulation and going in and out, letting him/your hands do all the work and and riding him/ pushing back on his cock.
There is no one best way to get fucked, change is your best friend!
Chapter 6: Multiple Orgasms

Ok, so now you are able to cum like a girl. But can you cum as often as they do? Unfortunately not all women will ever experience this and neither will all Sissies, but I’ll do my best to help you get there.
Basically I taught you all the tips to increase your pleasure in the last chapter already, but if you don’t experience multiple orgasms yet follow these additional tips:
1) Neglect your clitty
If you didn’t already, stop touching your clitty, don’t let it get hard and don’t let it ejaculate. And I’m not just talking about during your fucksession, but all the time! The more you wank or even get hard the longer it will take for your body and brain to stop associating pleasure with your clitty and start shifting your erogenous zone into your pussy.
If you are having trouble with this follow my clitty guide.
2) Work on your stamina!
Sex is a great workout and like any workout you do you’ll be able to do it longer the more often you do it. If you are out of breath after 5 minutes of fucking it will be hard to manage multiple orgasms. Take up some sporty habits. Go jogging, swimming, biking. Take the stairs instead of the elevator/escalator. Anything helps.
3) Pause
Sure, you can fuck your brains out in one quick ride and have a great orgasm, but why don’t you try stretching your fucksessions a bit? Don’t just use that dildo as a tool to get off, make love to it! Take your time, reach pleasure, then pause. Leave the dildo in your ass and cuddle your pillow or something. Then go on.
Chapter 7: The Plateau

So you probably heard of "edging", but in case you didn’t it is when a man wanks his penis and stops before he cums. He’ll do this again and again to prolong the pleasure.
A similar technique can be applied by Sissies. The only difference: Sissies don’t reach an edge they can fall over, but instead a plateau that you can stay on or reach again and again.
I often have multiple orgasms and sometimes I’ll actually stay on that plateau for a while, meaning: My orgasms take longer and longer until the last one only stops if I am too exhausted to go on.
I sincerely wish everybody can have this experience some day.
Chapter 8: Extending Erogenous Zones

By now you probably realized that there are many different types of orgasms and that they can be reached in different ways. There is the short pleasure of ejaculating after ferociously wanking your clitty for a minute, there is the long lasting, deep and sensual pleasure of getting penetrated that will make your heart pound, your muscles spasm, your whole body shiver and melt your brain away and there is a spectrum in between.
Basically an orgasm is the loss of control over parts of your body and/or body functions (like holding back your liquids) combined with pleasure.
So why should that only be reachable by genital stimulation? It’s not!
Genetically speaking your pussy is not a real pussy – so it’s not part of your genitals, but you trained it so now it practically is one.
You can do the same with your throat! Getting fucked in your mouthpussy has all the same requirements to reach an orgasm like when getting fucked in your asspussy:
- it’s both painful at first
- you have reflexes that make you push out whatever is pushed in on either end
- it’s basically the same material – mucosa of your alimentary tract
- you have glands on both ends that can produce slime upon stimulation (prostate and salivary glands)
The bad news: Deepthroating and especially learning to get pleasure out of it is even harder than learning to take it in the ass and loving it.
The good news: I’ll write a guide about Deepthroating sooner or later.
Chapter 9: The ultimate Sissygasm
Keep reading if you think you can handle it!

Ok so since Chapter 3 I taught you how to increase your pleasure. Now let’s get back to the question from chapter 2: What is a Sissygasm? What is a real Sissygasm?
To answer that once and for all we have to first ask ourselves: What is a Sissy?
Well there are tons of different definitions, but one thing most of them have in common is: Sissies are submissives that are supposed to put their dom’s pleasure above their own.
So what does that mean for Sissygasms? Wouldn’t that mean a Sissygasm is simply when the Sissy’s dom has an orgasm? Isn’t a Sissies ultimate goal not her own pleasure but making her master cum in her mouth & ass or licking her mistress into nirvana? Well, yes!
So if you have a dom and you want to be their perfect Sissy forget everything I just taught you and simply do whatever feels best to them!