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April 2017

ItsyBitsySissy’s Ultimate Sissygasm Guide

itsybitsysissy:

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!

Keep reading

Apr 21, 2017 29,150 notes
ItsyBitsySissy’s Clitty Guide

itsybitsysissy:

This guide will teach you how you get a clitty as tiny, limp and useless like mine. I will guide you through the phases I went through and will update it later with the phases I have not been through yet.

What can you expect?

Depending on where you start and how much discipline you show you can reach the stage I’m at now in a few months up to one or two years. The result will be a constantly limp, tiny and quasi-impotent clitty, shrunken and idle testicles (I call them ovaries) and a reduction in your testosterone level.

All of that without taking any hormone replacements or other medication! I will now start hormones soon which will be the next phase. If you already take hormones or start at an earlier phase than I do you’ll reach your goals faster.

In general the phases don’t have to be walked through in a strict order. You can mix it up and even leave some parts out. On the end of the guide I’ll add a summary of all the practical tips to shrink your clitty.


Phase 0: On the Edge


About this phase:

So you’re a pathetic wanker are you? You may be a looser virgin who has no chance with the ladies, a tiny dicked horndog who could never satisfy a woman, a life-long inhabitant of the friend-zone or a hubby of a bbc-hotwive.

Whatever the reason: Your sexlife is comprised only of wanking and porn. It’s probably been like this for a long time, you’ve been through all kinds of porn and only increasingly perverted kinks satisfy you anymore.

You love captions that humiliate you and lead you deeper into your fetishes. You are a gooner who edges to pics of big cocks, small cock humiliation and sissy porn.

You’re on the edge - the point of save return. If you manage to tame your sick urges now you may go back to leading a “normal life”, but do you really want that. Wouldn’t you much rather give in fully and take a leap of faith?


Tips:

Excessive wanking can shrink your penis, but only with moderate success. Depending on what you consider excessive it may actually increase your size.

One way to improve results is to suppress bloodflow to your thingy during erections. You can do that by bending it back towards your ass. This will hurt the first times you do it and may not be a suitable position to keep during wanking. Instead you can do this when fully erect to kill the erection and prolong your edging session.

Alternatively you can dry-hump your pillow or mattress in a way that bends back your penis in the same way. This way you can wank hands-free.

But as I said you can’t expect very promising results in this phase, so you better go on.



Phase 1: Accepting your fate


About this phase:

After some time being a pathetic, porn-addicted looser you have to finally accept that your penis is a disgrace and not meant to be used. Not only is it not meant to satisfy women, but you are actually not supposed to wank it either.

Wanking is for real men, not for sissies like you. You really have to suppress your addiction to give yourself pleasure that you don’t deserve.

You know this, but you still can’t stop yourself from wanking.

Your goal in this phase is to deepen your acceptance and reinforce your determination to shrink your clitty and become a sissy.


Tips:

Find ways to keep yourself from wanking.

Try chastity, cold showers or satisfying yourself in other ways. (=anally)

Watch lots of sissy hypnos, follow sissy tumblrs and avoid watching straight porn. Don’t look at vaginas and never identify with the man. Also avoid big-cock-tranny porn as that just confuses sissies.



Phase 2: Betabating


About this phase:

Ok so you accepted that you shouldn’t be allowed to wank, you should do everything to shrink your clitty, but your flesh is too weak.

You can’t fully give up wanking yet, but at least you’ll have to follow these rules now:


Tips/Rules:

You are only allowed to wank with 2 fingers

You are not allowed to wank to naked women

You should always have something (dildo, plug) in your sissy pussy while wanking. If you don’t follow this rule you are not allowed to cum by any means.

Whenever you ejaculate cum you’ll have to eat it all up.

Try to learn to cum from anal stimulation. Then try to do so without using your hands to help. Then try to do so without getting hard and if you manage to do so try to have orgasms without ejaculating.

Do that by not pointing your dildo towards your prostate but instead deeper inside your guts. Gurls cum without “cumming” and it’s much more pleasurable.

If you can’t cum like that by the end of this phase that’s ok. You’ll learn in Phase 4 at the latest.



Phase 3: Chastity Fetish


About this phase:

This phase can be skipped if you manage to reduce your wanking frequency without chastity. If you’re still addicted to wanking get a small chastity cage and wear it as much as you can.

Chastity is great way to learn resisting wanking in a kinky and playful way. If you have never tried it before I’ll tell you what to expect now.

When you wear a chastity cage and get horny/hard it will hurt - especially the first times. Take the cage off if it hurts too much and try again later. The chastity cage will keep you from becoming fully erect, but it will not keep you from feeling the satisfaction you usually feel when you have a hardon.

Actually you’ll soon find that wearing a cage gives you a special kind of satisfaction. You’ll learn that looking at humiliating captions while being locked up is a better feeling than wanking.


Tips:

The chastity fetish will usually not teach you to reject your penis. Instead your pleasure will be even more centered around your penis. That’s ok at first, but at some point you’ll have to start really focusing on your sissy pussy.

Try to make your chastity sessions longer and longer. When you get too hard go for a walk, take a cold shower or fuck your brains out with a dildo.

Fucking your sissy pussy will make your clitty get limp and you’ll be able to stay chastised longer.

Try to wear your cage over night too. Many genetic men tend to have nocturnal erections. Try to reduce them!



Phase 4: Learning to Tuck


About this phase:

Ok now let’s get serious. You’ll have to learn to stop wanking altogether.

Actually try to avoid getting hard at all causes.

These tips will help you:


Tips:

1. Tucking

Learn to tuck! Tucking is more effective than chastity. In a chastity cage your clitty is kept from getting hard and big, but your balls are free and unrestricted. Your balls are the producers of sperm and testosterone and if you lay down and watch them you can actually see them work. It looks a bit like they are breathing - so now we’ll try to suffocate them!

Try to push your balls past your clitty towards your belly, so that your ballsack is empty. This sometimes happens on it’s own when it’s really cold or when you feel very deep satisfaction (usually from anal). If you can’t do this at first lay down on your back, raise your ass in the air and try again.

Now with your balls tucked away move your empty sack and limp clitty towards your ass - the further back the better. Use one hand to hold your “tuck” in place and with the other one pull up your panties. I like to use multiple layers. As the first layer I prefer girls’ cotton-boxerslips. They should be tight, but at the same time wide enough to cover everything.

Next layer should be even tighter and elastic. Bikini Bottoms are good, but even better are sport-tights/shorts. They will keep your tuck in place without any tape needed.

While tucking there are some different forms of pain you will probably feel: Pressure on your ballsack or clitty can be caused by using too tight panties or by having done a sloppy job tucking. Untuck and try again when the pain is gone. You can also feel pain or paraesthesia of the skin of your outer thigh. This is a result of too tight panties which compress a nerve. Untuck right away and let the nerve regenerate. To avoid this use wider panties next time and make sure the individual layers don’t tangle up. Only tuck again when the pain is fully gone!”

The next and worst pain is the kind where it feels like your balls are bleeding or your sperm-duct is cut off. This is your balls complaining about the decreased blood-flow, which is exactly what you want. But still untuck when you feel this pain. Let your balls regenerate and try again later. This pain will come later and later with every tuck and eventually fade away fully.

2. Real Sissygasm

Your goal in this phase is to be limp as much as possible. When you get horny and hard you’ll have to do something about it. Your wanking days are over, so now you’ll learn to only get pleasure from anal play.

If you don’t have one yet get a nice, big, curved dildo with realistic structure and a suction cup. Ride it whenever you feel horny while pointing it towards your back - away from your prostate. If you’re doing it right your clitty will not get even a little bit hard this way and you will not ejaculate anything more than a little precum.

Alternate speed, depth and position to increase your pleasure. You’ll start to shiver and spasm and it will feel like heaven on earth. Doesn’t that feel much better than all orgasms you ever had before? And what’s even better: You can have multiple orgasms this way, just like a real girl!



Phase 5: Tucking all day


About this phase:

The goals of this phase are very simple: tuck all day! Give your little thing no freedom, and make sure your little gonads stay inside all the time, just like ovaries!

You can only loosen your tuck while sitting on the toilet (try to keep your ovaries tucked with one hand) or while getting fucked/riding your dildo. Even at night you should stay tucked to teach your body not to have nocturnal erections (you may not even know you are having them if you never tried tucking or chastity over night).


Tips:

If you do long time tucking you’ll have to look out for your genital hygiene or you’ll sweat so much that you create a perfect habitat for all kinds of bacteria in your pants.

3 simple tips: Only let 100% cotton touch your skin - no synthetic fibers!

Use baby-powder! Go for one that’s not packed with chemicals or even better: Use organic Rhassoul powder.

And the obvious one: Shower and change your panties every day!

Also, when tucking for a longer period, you’ll learn which of your panties and sports bottoms are providing more security than others while still being comfortable. Use that knowledge wile buying new stuff and go for even tighter things from time to time. You can also get some tight jeans or jeans-shorts to wear over your tuck (and under your boy-costume) to provide even more security.



Phase 6: Quasi-Impotence


About this phase:

This is the phase I’m in now. I’m tucking 24/7 and my clitty never has the chance to get hard. I can’t even remember my last erection.

I’m quite sure I’m not permanently impotent yet. If I were to stop tucking I’m sure after some time I’d regenerate the “abilities” to get hard and to ejaculate.

But it’s like a diet: If you just eat vegetables for 2 weeks to loose some weight then you’re not vegan. To be vegan you have to chose to avoid animal products forever. I’m vegan and since I decided to tuck for the rest of my life and never have an erection again: I am impotent!

I have totally lost any urge to masturbate like a man. I still get horny, but my sissy-pussy is the thing that twitches and wants to get fucked, while my clitty stays limp and lifeless.


Warning:

Teaching your sexual organs to stop functioning will decrease your testosterone production. So at this phase you should really start seeing medical professionals and talk to them about your transition plans.

If you don’t want to go any further you should at least schedule frequent blood-checkups to make sure you don’t reach a dangerously low hormone level.



Phase 7: Hormonal Changes

This phase is about to start for me. I’m probably just a few weeks away from getting approved for hormone replacement therapy and I will update this guide and share my experiences.

I can’t and will not give any legal or medical advice however, so please double check everything with your doctors.


Phase 8: Orchiectomy


This phase has no date scheduled yet, but it’s a definite thing I’ll do in the future. Check back for future updates.



End notes:

Thanks to everyone who donated or helped/helps promoting this guide by reblogging.

All donations I receive now already count for the next guide:


        💝💝💝💝💝💝

         💝 Donate 💝

       💝💝💝💝💝💝


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Apr 21, 2017 12,705 notes
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