How Do I Masturbate Like a Sissy: A Crossdresser’s Guide for Self Pleasure


As a sissy, I am going to share a very personal experience that I feel whenever I feel like masturbating.


See, as sissies, we all deserve sexual pleasure, but due to the lack of information about the sissy masturbation technique, most of us are devoid of the sissy fun.


 Like a Sissy


In this guide, I will tell you how you can masturbate like a sissy and feel heavenly sissygasm, multiple orgasms, and femininity.


Get lubed up, and let’s get started.



What do I mean by Masturbation Like Sissy?




Alright, so you want to know what I mean by masturbation like a sissy, right?


So, there are mainly two ways in which you, as a crossdresser, can provide yourself with self-pleasure.


One is the boring and monotonous method of stroking the penis and finishing quickly.


Babe, if you’re still using that technique of masturbation, you’re missing out.


As sissies, we’re special, so we have unique ways of masturbating to achieve sissygasm, which is masturbating like a woman: creating a scenario, dressing beautifully, engaging the entire body, and enjoying every sensation.


Sissies masturbate like women, not men. Keep that straight in your mind.


There are different toys, hand techniques, pleasure points, and feelings involved.


We’ll discuss the techniques and the feelings associated with sissygasm later in the blog, but first, let me clarify any confusion about whether crossdressers can experience sissygasms.


Can Crossdressers Have Sissygasm?




Indeed, If I’ve enjoyed sissygasm, surely you can as well.


Being a crossdresser allows you the thrill of a sissygasm.


Yet, reaching that special sissygasm? It’s a tad different from the regular orgasm.


To grasp that feeling, you’ll need to adopt a more delicate, feminine approach to self-pleasure.


And hey, when I mention “different,” relax—it’s very simple to grasp.


How Sissygasm for Crossdressers Differ from Normal Orgasm?


sissy masturbation


Sissgasm is different from normal orgasm because for many reasons.


The first reason is the sexual need of a sissy is different from those of a normal dude.


While a normal man is chasing that finishing orgasm, a sissy is more about feelings and investing emotions to build up to sissygasm gradually.


A normal orgasm is simple, achieved by a monotonous action of stroking the penis.


At the same time, the process of sissygasm is completely different, and it involves a series of different actions and techniques that lead to a sissygasm.


The traditional orgasm is more about the body and physical touch, while in the sissygasm, the mental zone, mood, and surrounding atmosphere play a very important role.


A Crossdressers Guide  


Another thing is that the toys involved in sissygasm are unique and different, such as chastity cages, dildos, nipple clamps, etc.


Toys which ignites the feminine feelings in sissy men. While in normal orgasm, Ha, what do I tell?


No toys are needed. Sissies can’t live like this, right?


Normal orgasm is a more masculine style of orgasm, which happens quickly and one time, while sissygasm is more feminine, and as a sissy, you can even experience multiple sissygasm.


I am not even kidding.


Now you know what you are getting into, let me tell you how to prepare for a sissygasm session.


How do I Prepare for a Sissy Masturbation Session?


How do I Prepare


I know you all have been waiting to know my process, and don’t you worry, girl, your big sissy got you when it comes to preparation; l like to keep things very simple but also very glam.


Dress Feminine


That’s where I start when I feel like indulging in some self-pleasure moments. What do I wear?


I usually choose sexy pajama sets that are both comfy and feminine.


It’s easy to move my hand and body in pajamas.


Hmm, you know what I mean.


Since I like to go all femme, I shave all my body hair and paint my nails to have that extra “cutie pie” feeling.


I also apply minimal makeup to feminize my face.


Why do I do this?


You’ll find out later. I’m quite kinky, babe. Haha!


Dress feminine


Find a Comfortable Spot


The most important consideration for me is the location where I have my personal, romantic moments.


I ensure it’s comfortable and cozy, allowing me to switch between multiple positions.


I also ensure there’s a large mirror in front of me so I can watch myself while having fun.


Now you understand why I like to feminize my face.


It’s a heavenly feeling for a cross dressing sissy.


You should give it a try.


Take My Toys


I keep my boys— I mean toys—near me.


That way, when it’s time, I don’t have to leave the spot to find them.


All of them are ready to satisfy their lady.


Sissy sex 


Feminize My Mood


I treat myself special, and you should do that, too.


What I do is add some good fragrance in my room, dim my lights, and pour myself a glass of wine with some sissy hypnosis for at least 30 min.


Remember I told you to take things slow.


Techniques I Use to Masturbate Like a Sissy


jerking off  


Refrain Jerking-Off


Here’s the thing.


You call yourself a sissy crossdresser and want to have fun like a sissy.


Stop jerking off. Yeah, that’s what I do.


Refrain from ejaculating at least three days before for a good experience.


You can also lock your clit in a sissy chastity cage to control urges.


And when the time comes, avoid stroking and do it in sissy style.


What’s the sissy style?


Apart from stroking your penis, everything else is sissy style.


For example, rubbing, humping, and grinding.


When it comes to rubbing, rub like a woman.


I use my fingertips and the palm of my hands to please my sissy clitty.


I usually have my panties on as it provides extra smoothness.


It’s a feminine thing to do being a sissy.


You can also rub your gooch, a very sensitive area, b/w your balls and ass.


Rub it in a feminine style like the way ladies do, you know, with the two middle fingers, slowly, just rub, lying on your back, knees up.


Yes, girl, that’s the way to go like a pro sissy.


Another technique is grinding like a sissy using the palm of your hand.


I sometimes stuff a pillow b/w my legs and grind, straddle the pillow and press my clitty into it and just hump and grind, feeling that sexy sensation building already!


Change Positions


changesex position 


Yes, changing position is very important to feel every sensation. I frequently change position every 15 min.


Here are some of the positions I try while masturbating.


Humping and grinding on the pillow


Very simple position; you sit on a pillow or any stuffed toy of yours in a cowgirl style and just hump over it.


This is how I do it. I make sure there’s a mirror in front of me.


When I am humping or grinding, I like to go commando, meaning wearing nothing.


I feel the sensations down there and moan a lot to intensify my feelings.




Spooning is my fav.


Just do nothing.


Lay on one side, put your hands in panties, and simply rub.


Close your eyes and play a sissy hypno for a better experience.


That’s what I do, and it works for me.




Doggy style leaning


The best position for both anal and clit stimulation.


Come on, your all four like a doggy and take your one hand to your clit and simply rub.


For added stimulation, you can insert a vibration butt plug or dildo in your butt.


After a point, you might feel tired so you can rest your head but still on your knees.


A very vulnerable and sensual position.


You’ll love it.


Inverted doggy style with knees up


In this position, you are on your back and knees up.


Literally no weight on your body.


It’s one of the most comfortable positions where you can channel your energy on sissygasm.






If your leg strength is good, then this makes for an excellent masturbating position.


It opens up your legs as if you want penetration and makes you feel feminine.


The sissygams at this moment can be massive.


Well, these are some of the positions that I try.


There are many more masturbation positions that you can try.


Use Sissy Training Toys


Sissy orgasm 


There are various types of sissy training toys that you can use to achieve sissygams.


Different toys have different characteristics and functions, which you can pick as per your own needs.


Sissy training toys are a great way to experiment with different sensations and discover your sexual preferences.


Here’s a list of sissy training toys.


Butt Plugs


Cock Cages or Chastity Cages

Chastity Belts


Anal Beads

Sissy Clothing

Breast Forms


To understand more about sissy training toys, read “Top 9 Sissy Training Toys for an Exciting and Fulfilling Experience.


Moan Like a Sissy


A sissygasm feels a bit, well, unfinished if you don’t let yourself moan at the moment.


There’s something about moaning that brings out that inner horny girl in you.


Plus, it makes the whole sexual experience more lively and steamy.


So leave the shame; let out those moans like you’re having the last sissygasm of your life.


Moan likw a sissy


Finish in Style


Guys often finish in such a dull way and then just feel kind of blah afterward.


But us sissies?


Well, I can’t speak for everyone, but I love giving myself a facial.


A hot, wet facial.


There’s something about it that just amps up the sexiness and leaves me feeling truly satisfied.


If you’re not into the whole facial thing, at the very least, have it on your stomach.


It’s just a sissy thing, you know?


What Do I Do Once I am Done?




After I’ve wrapped things up, I just kind of chill on my sofa for a little while, soaking in the feels.


Then, I stretch out a bit – nothing too wild, just a quick one to ease my back, legs, and thighs.


Next up? Clean-up duty. I’m all about leaving no trace behind, so I tidy up the area and make sure everything is spotless.


And my toys?


Have to keep them clean and ready for the next go-round.


Once all that’s squared away, I hit the shower – a good, long one.


It’s the perfect reset, and then I’m off, getting on with whatever the day has in store.


Final Words



Self-pleasure or masturbation, whatever you want to call it, is an essential activity that leads to sissygasm, and we all know that sissygasms are an essential part of a sissy’s life as it helps in reducing a lot of physical and mental stress.


The process of it makes you feel feminine and makes you understand how it is to have a feminine-like orgasm.


You can follow my techniques and add yours, too, to achieve a true sensual experience.


Make sure you share your techniques and help fellow sissies.


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