Sissygasm Tips, Tricks, and Techniques
Hello girlies! I am making this post as a reference guide so I have something to link people to when they ask me “how do I have a sissygasm?” because you horny girls never stop flooding my inbox with questions ☺️ I thought a Q&A style format would be good so I can cover the most common questions and you can find answers if you’re looking for something specific! Please keep in mind that this is what I’ve found works for me, and the results may vary for you. Getting to know your own body is one of the most important parts of achieving a sissygasm. I have many years of experience with anal and learning my body. I organized the questions into sections that made sense to me, so let me know if you’re getting stuck at any particular spot.
EDUCATION PHASE:
What even is a sissygasm?
This is a term that is thrown around a lot in our community, and it is commonly used as a catch-all term for multiple things. The most commonly accepted definition is cumming from anal penetration without any form of clitty stimulation, but I have also seen “sissygasm” used to describe prostate orgasms, any hands free orgasm, and orgasms while in chastity. For the purpose of this guide, I will be referring to sissygasms explicitly through anal and prostate stimulation as I have found these to be the most enjoyable.
I’m brand new to being a sissy and anal, how can I have a sissygasm?
This is one of the most common questions I get. If you are brand new around here, you aren’t just going to be able to snap your fingers and get a sissygasm. It’s something that takes time, practice, and lots of patience. Nobody ever got a sissygasm on their first try. It’s something that can take weeks, months, or years to learn depending on how much you practice and how committed you are. If you clicked on this guide looking for a magic bullet, you’re not going to find it because it doesn’t exist.
What does a sissygasm feel like?
I’m not saying this to brag or to rub it in for anyone that hasn’t had one yet, but it is the most incredible physical sensation you will ever experience in your life. Your brain is flooded with the most overwhelming sense of euphoria, and it radiates through your entire body like a tidal wave. It is incredible and you will know it when you feel it. Once you have a sissygasm, you will never want to go back to jerking off like a boy again, you will be broken.
Where can I find more educational material?
I learned a lot from r/proststeplay and r/sissy . I linked some of their informative material below. I will post more links here if I find any more good ones in the future. Please feel free to share links with me if you know of any other good guides!
https://reddit.com/r/prostateplay/wiki/index
https://www.reddit.com/r/ProstatePlay/s/hJuVFasgen
https://www.reddit.com/r/Sissy/s/wzzNUeH3ZB
https://www.reddit.com/r/Sissy/s/hEDRHZiMm7
https://www.reddit.com/r/Sissy/s/x4hbGlbt6U
https://www.reddit.com/r/SissygasmSchool/s/sXXw6NU6gn
PREPARATION PHASE (pre-anal):
How can I mentally prepare?
I cannot stress this enough - MENTAL PREPARATION IS JUST AS IMPORTANT AS PHYSICAL PREPARATION!!! Having a sissygasm is just as much a mental experience as it is a physical one. Before you even start your anal session and try for the sissygasm, you need to be in a clear, relaxed, and feminine head space. Imagine putting yourself inside a pink bubble where you are the perfect sissy and nothing bad can happen. Do whatever you need to do feel as relaxed and feminine as possible. If you are stressed, annoyed, or frustrated, you’re doing it wrong and you should try again another day. This is supposed to be a relaxing and fun experience, so let yourself have fun and don’t stress about it.
Do I need to dress up in feminine clothes?
This is part of the mental preparation. If dressing in something cute, painting your nails, and doing your makeup helps you relax and feel more feminine, then please do that if it helps you get into that pink bubble head space. It is absolutely not required though, so don’t feel like you have to do this.
Do I need to wear a chastity cage?
This also goes with the mental preparation. If wearing a cage makes you feel more feminine and relaxed, then wear one. Remember that for the sissygasm we are going to be focusing entirely on the ass and the prostate. Your little clitty will not be used at all during the process. If you think you will be distracted and want to touch yourself there, I would recommend locking up. If you have the discipline to not touch your clitty, then you are ok to proceed without one. Either way it’s not a required tool, but it can certainly help.
Do I need to use poppers, weed, or alcohol?
I know I sound like a broken record here, but it goes back to the mental preparation and the pink bubble. Are they required? Absolutely not. I don’t personally have any experience with poppers, but I have used weed and alcohol multiple times to help me relax and get into a good head space. I have also had plenty of sissygasms without them, so don’t feel like it’s something you need to use if you aren’t comfortable with it or don’t want to.
Do I need a partner to help me?
No. Sissygasms are something that can be achieved all on your own. That being said, don’t be shy about including your partner once you’ve learned the ropes.
Should I watch hypnos or porn before I get started?
Maybe. If this is something that helps you get into the pink bubble head space, then go for it. I find that watching certain hypnos gets my clitty too aroused and can be detrimental to me focusing on my ass. I personally like to listen to really feminine/sexual music (without visual stimulation) before an anal session because it sets the mood without getting me overly aroused. This is one of those things that you have to figure out what works best for you!
How can I manage my surroundings to help me?
This is something that often gets overlooked entirely. Do yourself a favor and create a nice space for yourself for making love. Clean up your surroundings, light a candle, make sure the room smells nice, use a clean set of sheets or towels, dim the lights down low, and act as if you’re getting ready for sex. This will really help your mindset and make the experience more enjoyable. Again, not a requirement, but it can really help.
What kind of toy should I use?
I find that normal silicone dildos work best for me. Not prostate stimulators, not vibrating toys, not butt plugs. Just a normal penis shaped dildo. That being said, I have a much easier time getting a sissygasm orgasm with larger toys. The larger the toy, the more pressure you can put on your prostate, and thus the easier it is to achieve the sissygasm. I will warm up with smaller and mediums sized toys and gradually work my way up to my biggest one. My largest dildo that gives me sissygasms so easily is about 10 inches long and 2.5 inches wide (yes, I’m a size queen). I recommend finding a toy size that is comfortable and feels good. It’s not a competition, it’s a personal journey to find what works for you.
Should I abstain from cumming for a few days before trying?
Maybe. Most sissies would agree that this can help, but it isn’t required. If you don’t cum for a few days prior to your anal session, you are more likely to be extra horny which may help push you over the edge, and you might have a fuller tank that is more ready for a release.
ACTIVE PHASE (during anal):
Should I watch hypnos or porn during my anal session?
Maybe. Your primary goal while you are fucking yourself should be focusing on and listening to your body and the pleasureful sensations. I find hypnos, porn, and even music can be too distracting for me when I’m actively trying to have a sissygasm. When I want to listen to something, I put on the sounds of rain, the ocean, or anything with a peaceful, euphoric, and non-distracting ambiance. If you can watch porn and focus on your ass at the same time, more power to you.
Should I be thinking about a fantasy?
Maybe. This is something that really helps me get into the mood and enjoy the moment more. I think this goes hand in hand with the mental stimulation that I mentioned above. Imagine you’re getting your ass fucked by someone (or something) that really really excites you! This is where drugs and alcohol can help if that’s something you’re interested in. I find that using weed/alcohol helps my fantasies feel more realistic if I close my eyes and just zone out into that pink bubble and my fantasy. This is not something that is required though.
What if it hurts or I’m uncomfortable?
If anything hurts or is uncomfortable, stop immediately. No part of this process is meant to be painful. If you need more lube, use more lube, it’s that simple. In my experience you can never ever have enough lube. If your toy is too big, try warming up a little bit more, but don’t force it. There is absolutely no reason to hurt yourself for this, it’s supposed to be an enjoyable experience.
What position should I be in?
There is no right or wrong position to achieve a sissygasm, however I have found some positions are easier than others. Getting to a full blown sissygasm can take anywhere from 5 to 10 to 15 minutes depending on the person and level of experience. The name of the game is finding a position where you won’t get tired out too quickly. I have found that any position that requires me to do a lot of motion with my hands or arms gets me tired our really fast, so I won’t have the stamina to push for the sissygasm when I get close. The best position for me is doggystlye with a suction dildo mounted on a wall, that way I can easily ride my dildo without getting myself tired. I have also found that putting my toy up a little bit higher helps, that way when I push back on it, it’s angled in a way that puts more downward pressure on my prostate.
What should I be doing during my anal session to help?
For the first few minutes, just take some time to get yourself warmed up and loose. Enjoy the sensation and do whatever you need to make yourself feel good. When you are ready, there’s is one trick that I have that help. I know I said that there is no one magic bullet for getting a sissygasm, and there isn’t, but if there was one thing I would recommend everyone try, it would be this: kegels. A kegel is the technical term for when you clench your asshole muscles. When you do a kegel while you have a toy inside you, it’s puts more pressure on your prostate. And as I mentioned before, the bigger the toy, the more pressure you can apply. Start by getting your toy in to a comfortable and pleasurable spot. Try holding a kegel for 7-10 seconds. You can still ride your dildo if you want while you are holding the kegel, but if you do, I would recommend going nice and slow. If you just want to be stationary, that’s totally fine too. Do whatever feels good. When you finished holding your kegel, take a 3-4 second brake to catch your breath and rest. Then hold another kegel for 7-10 seconds, then rest again. The number of seconds is not important, it’s just a suggestion. Find a rhythm that feels good for you. Repeat this process again and again and eventually you will start to feel a pressure building inside your ass. It might feel weird, but don’t stop your kegel rhythm. Eventually, you may want to hold your kegel for longer than 10 seconds if it starts to feel really good. You might find that the harder you kegel, the better it feels (because you’re applying more pressure). Feel free to still ride your dildo slowly while you are doing this if you like, we are giving that prostate a nice relaxing massage. After a few minutes of this kegel technique, that pressure in your ass will start to turn into crazy pleasure. When this happens, hold your kegel for as long and hard as you possibly can, you are about to have a sissygasm :) if you hold your kegel really really hard in the right spot, you will get incredible waves of pleasure coursing through your entire body. Don’t stop holding your kegel while this is happening!!!!!! The pleasure will stay there as long as you hold the kegel, so hunker down and enjoy the ride!!! Some girls will cum from this and some won’t, it seems like results vary from sissy to sissy.
What if I did everything you said and I’m still not having a sissygasm?
This is a very common question. As I said before, nobody ever gets it on the first try, and maybe not even the tenth try, and that’s ok. This is a process where we learn about your body and your mind, not something you can try on a whim. It’s very important to not get discouraged, not get frustrated, and not give up. We don’t let those negative emotions into our pink bubble head space. If you’re tapped out for the day, come back again another day when you’re ready and in a better headspace. Unfortunately with sissygasms, it seems that the harder you try, the more elusive they are. I encourage you to focus on enjoying the way your body feels and enjoying your pink bubble headspace rather than hyper fixating on a specific goal, and the sissygasm with come to you in time. If you come crying to me saying “why isn’t it working???” I’m probably going to ask you the following questions:
Did you actually read my post???
How long have you been trying?
Were you fully relaxed and calm?
Were you rushing or being impatient?
Were you actually enjoying the experience?
Were you distracted by something else going on?
Were you having pain or discomfort?
Please reflect on these questions if you still need help
What do I do after I have a sissygasm?
If you are lucky enough to get one, there’s no reason why you can’t repeat the process. I am able the have multiple sissygasms in one session, usually only about 5 minutes apart after you get the first one. The biggest limiting factor is how much they will tire you out. I can usually go for about 30-45 minutes before I’m absolutely exhausted.
That’s the end of my Q&A!!
I will keep this list up to date as more questions come in. I hope this helped you and please feel free to reach out or comment other questions you have! Have fun girls!!!
Amy 🥰💕