Achieving a hands free anal orgasm(sissygasm) can be a challenge for most girls. It can take time, patience and training. Here are some tips and tricks from sissies who've gotten over the hump and are now able to cum like a girl.

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Original Post on reddit.com/r/girlschool

Okay, so I've actually gotten quite good at this, but I've never attempted to write it up. Fair warning...I'm a sissy and I write like one. SorryNotSorry

Step 1) Don't cum for at least 2 days. I find that 3-5 is ideal for me. Just like having wet dream is due to a build up of semen in your system, you want semen and sperm to build up to create more pressure on the prostate so you can cum from anal stimulation.

Step 2) Get in the mood. Cumming from anal is - so I'm told - actually a lot like cumming when you're a woman. It's more of a mentally driven orgasm that requires your mind to be free of any other thoughts.

I like to get dressed up in my sissy attire, put on porn, take pictures of myself and post them, flirt with guy online, etc... all without EVER touching my clitty or pussy. If my clitty gets hard, I just eat my precum and ignore it.

Step 3) Ease into it. I know you said you can fit two fingers in your butt and move them in-and-out, but don't jump straight into fingering. Play with your hole. Feel how the tickles transform into pleasurable touches.

Step 4) Mount something and ride it. I find that I can't cum from in-and-out fingering or toying. I need to ride something cowgirl style . This allows for two things: ideal position for prostate simulation, and for my clitty to grind on something.

Step 5) Kaboom!

Also, during steps 2 and 3, really focus on periodically squeezing your orgasm muscles (sorry, idk the technical term...). The pumping will help create more semen and help your prostate to start swelling.

Good luck!

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Original Post on reddit.com/r/sissyhypno

Hello there girls ! : *

I know a lot of you are trying to reach that dreamed sissygasm from hypnos. As someone who struggled and took lots of time to achieve that, I feel that I should share with you this information... it works magically for me and I hope it can help someone else.

So, when I got my first sissygasm I used to follow this routine with my hypnos:

- Dress up (optional)

- Put a good hypno playlist (of course)

- Lube up, light anal play just to loosen up.

- Light up some weed *

- Intense dildo anal play**

This combination was already fairly strong and you can already achieve the sissygasms (dry and/or wet) and milking without much effort using only anal stimulation.

But recently I added two things to the recipe that were total gamechangers:

- A VR headset (a Google Cardboard with your cellphone will do and I recommend using Bluetooth headphones with it)

- A hitachi magic wand (It allows me to get a clit/perineum stimulation while staying limp... I find it very girly, I just put it inside my panties so I get a free hand and I get less tempted to stop the orgasm by reflex)

OMG Now it's orgasm after orgasm after orgasm !!! This is simply waaay too powerful !!!

The VR headset gives you total immersion into the hypno (buy a good one, it's totally worthy) and combined with the weed you'll be tripping hardcore***. With a good VR set, your field of vision is just the hypno and nothing else and it's attached to your head so it's a massive improvement because you can't look away. It's like daydreaming, it's surreal... and it's overstimulating, it's like a sexual ecstasy.

I hope you all enjoy ! <3 XOXO,

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Guide to Achieving a Sissygasm - Original Post on Tumblr

1) Your prostate is a gland that has some involvement in storing semen. The reason why many people decide to practice edging or locking up in chastity is to accumulate a sizable amount of cum within the prostate. There are two reasons why this would be beneficial; the first reason is critical, an individual cannot, or will have a much more difficult time achieving a prostate orgasm because of the lack or shortage of semen in the prostate gland; simple stimulation of a “dry” or empty gland simply results in stimulation, climaxing however is much more difficult because there is nothing to release. Secondly, who doesn’t love the feeling of unloading a hot sticky mess that you’ve saved up for days or weeks?(; So try and refrain from masturbating or ejaculating for a few days before your sissygasm!

2) It is very crucial that you clean up and prepare ahead of time (preferably an hour ahead of time at the very minimum) before playing around with the prostate. I strongly recommend douching; the method in which I use to clean up is shower first, douche and hold in the water within my anus, and release any excess bowels and water on the toilet. Hop in the shower, douche again if you feel the need to, rinse and repeat until you feel your bowels are empty and no more feces appear in the released douching water. It’s also nice to wash your entire body with soap, remember, the preparation can be as exciting as the actual playing around itself, so enjoy pampering yourself. I find myself getting turned on removing any body hairs and running my hands across my smooth legs and butt, you should be able to as well!

3) (Optional) I like to smoke weed after cleaning up and prepping but before I actually play with my prostate. Now some of you may not agree with using marijuana, and that’s perfectly fine because it’s not necessary. I only smoke to help relax my muscles and intensify the stimulation I receive. If you do smoke weed, however, crank on some seductive music (or whatever you desire), relax (you’ll need to anyways since your anus needs a minor break from douching) for a bit, maybe even pick out whatever sexy clothes or lingerie you’re going to wear ;)

4) I cannot emphasize this enough, BE GENTLE, GO SLOW, AND USE A GENEROUS AMOUNT OF LUBE. It’s not a rush to achieve the orgasm as fast as possible, which is why a sissygasm would be a bad idea if you’re distracted or in a rush, so close the windows, put your phone on silent, and make sure no one will distract you; the purpose of a sissygasm is to relish and savor every second of the amazing stimulation.

5) Try and find comfortable positions and toys to use; I personally enjoy laying on my side as it is the position that relaxes my anal muscles. Once you get warmed up with a little teasing, you can move onto more stimulation positions such as cowgirl riding or even prop your dildo against the wall and ride it standing up, it’s all personal preferences. When it comes down to what toys to use, I strongly recommend something of smaller width and insertable length if you are a beginner (fingers aren’t a bad choice, just make sure they’re clipped and clean), there are various toys designed specifically for the prostate and come with a vibrating function that can help you achieve sissygasms much faster.

6) This is probably the most important emphasis of all, if your first or second time playing with your prostate did not result in a sissygasm, don’t give up! It took me until my 10th try (or even more than that) until I finally learned to relax, focus all my thought on my prostate (try doing Kegel exercises, but gentle ones), and let my hand and dildo do all the work.

I really hope this helps some of you, and if so, please reblog to help others learn how to achieve a ravishing orgasm that will leave you moaning and panting for more!

 

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Originally Posted on reddit.com/r/sissyhypno

If your sisspussy spasms and tries to push the toy out, just keep it in there and keep going. If you feel it building up inside then you're most likely on the right track, you just have to kind of 'let go'. I know for myself that I had a very big problem for a long time with worrying about accidentally peeing or what have you, but once I started accounting for that by peeing before play and making sure my sissypussy was clean, I managed to just focus on the feelings and not the consequences.

Another thing I would suggest is to kinda 'cheat' the first couple of times to get your body used to it. For example, the first few times touch your clitty (or your nipples if they're sensitive enough) while fucking your pussy, and basically edge. Once you're close to orgasming, stop and playing with your clit and keep going with your fucking your sissypussy.

There's also another sort of cheat which I actually really love doing. You do the same thing as above, but instead of playing with your clitty, you rub the spot right above the base of it like a girl would masturbate her clit. It provides a bit of pressure to help along plus it adds to the mental turn-on, which is an important part of actually sissygasming.

I love the idea of playing with myself like a real girl while penetrating my sissypussy :P.

There's also the possibility that the toy isn't really suited for that.

 

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Originally Posted on reddit.com/r/sissyhypno

You need to learn to enjoy anal. I know it’s been said countless of times but I can’t stress how important it is.

Find a dildo that’s not too big and not too small. If it’s too small you won’t feel enough, if it’s too big you can’t take it without hurting yourself. Same goes for a plug. Also get a second dildo, I’ll tell you what for later.

The length should be around 5-6 inches. The girth should be about 1,5 inches.

That’s good for beginners imo.

Start inserting a plug first, now make yourself beautiful. Dress up, do your make up, put on your panties so your plug can’t escape and now start edging by humping your pillow and watching the stuff that turns you on. I love watching huge, girthy, thick cocks, seeing them shoot a load makes me insanely horny. Now edge with the plug in your butt and stop when you’re getting close. This method makes you feel extra girly.

Do that for a few days, then do the same thing again and prepare everything.

Insert your dildo slowly while watching your favorite content. I recommend something with big cocks and big tits. Both together trigger something inside most sissies. I start watching Hypnos and looking at babe cock pictures. I imagine my favorite cock inside of me and then I just start riding the dildo slowly.

Use lots and lots of lube and try building up the pleasure. You don’t need to go gradually faster if the slow tempo makes you feel good, focus on that.

You will notice the pleasure going higher and higher, now you should go harder, not necessarily faster. Just harder. Your body will tell you what you need. Sometimes I need it hard and slow sometimes I need it really hard and fast. The longer I’ve gone without cumming the slower I usually can go and I will still have a sissygasm. If I came just a day ago I need it hard and fast.

When the pleasure builds up you shouldn’t stop so make sure to always have enough lube on your dildo. Ride continuously and don’t stop.

The feeling won’t go away unless you stop or get distracted so try to only focus on you riding that dildo, your naughtiest thoughts and your favorite cock that is just inside you.

If you notice that your getting closer and closer, and your body starts to shake try to clench your pussy, now ride as hard as you can while trying to imagine you wanted to make the cock spurt a load inside you cause you’re clenching it so hard. Ride it really hard now and shortly after you think you aren’t able to take one more stroke this one stroke will make you sissygasm.

Afterwards lick your mess up, get on your dildo again and keep your fluid inside of your mouth. Take another dildo and suck it as if your life depends on it and act like the semen just shot out of it. Meanwhile ride your dildo in a pace that makes you feel good.

Usually that makes me cum again.

Your mind plays an important role while doing all of this. Really try to not only focus on the mechanical part of riding also don’t let your thoughts just swirl around. Think about that hot cock you’re seeing right now. Think about the fat load you want so bad, think about everything that makes you horny.