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Some Ways a Sissy Can Masturbate 
As a sissy, there are multiple ways to masturbate to orgasm, and I thought we could discuss a few of them here. If you have any other ways that you stroke as a sissy, please leave a comment letting me know! I love hearing your personal stories and true confessions, and I know you’ll feel so much better sharing your secrets!
Humping to Climax
One way a sissy may enjoy masturbating is by humping against something such as a pillow. She could also use the arm of a chair or couch! To enhance the feeling of really having your clitty rubbed it’s best to be wearing a pair of slippery, silky, or nylon panties. Some gals choose to wear a pair a size too big so the fabric caresses the clitty even better. What’s interesting to note is that many cis-het ladies use the humping method to bring themselves to orgasm. The pressure builds, like going up an incline, and then you get to the summit and soar off into that orgasm.
If your bedroom pillow isn’t the right amount of firmness or softness that you need, experiment with other pillows in the house. Once you determine what you are looking for, you can purchase a pillow specifically for sissy humping. Cover it with a pretty pink slippery pillowcase, and you will be good to go!
One other position you may try is laying on top of your bed face down with your clitty against the edge of the mattress, with those silky panties on, and with your feet on the floor sort of bounce while humping against that edge. This is likely to work better if you have a larger clitty than most sissies, as the pressure will feel a little different. An itty bitty clitty just couldn’t slide enough to make this position productive!
Feeling the Vibe
Another way you can reach a sissy orgasm is with a vibrator. It can be small and powerful, or big and powerful. My two favorite toys are a LELO vibrator and my Hitachi Magic Wand. If you are just starting out playing with a vibrator I suggest something with variable speeds, so you can control the intensity of the vibrations until you know what works for you.
There are several movements or positions you can try to make the most of your masturbation session. One that will feel good is just a slow vibration being moved up your shaft, gently over the head, and back down again. If this isn’t enough, turn up the speed on your vibrator and see how that feels.
You can also place the head of the vibrator on your frenulum- the spot where your foreskin meets the underside of your penis. It looks like a small V just below the head. This spot tends to be very, very sensitive, so perhaps if you lower the speed of your toys when you begin to focus on this area you might not find the vibrations too stimulating!
You can also place the head of your vibrator against that tight smooth skin below your balls. It will vibrate the balls a bit, and also gently or intensely vibrate against the prostate from outside. Give it a try! I’m sure you will love it there. Basically, you can use your vibrator in any way that stimulates you. There are no hard and fast rules- just start out gently and increase the intensity as you become accustomed to the vibrations.
Penetrating Your Sissy Hole
This is a biggie! I first and foremost recommend lots of lube. Then I recommend some internal cleansing- Google it, please- “how to prepare for anal sex”! Then you and your trusty small to mid-size vibrator OR your prostate massager- will get in a comfortable position, caress yourself in all your erogenous zones, and then get that toy and yourself nice and slippery with that lube- make sure you keep a cloth nearby so your hand doesn’t get too slippery to hold on to your toy, though! Take it nice and slow as you penetrate yourself. You can even begin with a finger to help you relax.
Start with the toy either off or on very low speed. Insert it until you feel that you have reached that naughty p-spot. Then you can begin to slide the toy in and out a few inches and feel the vibration tingle through your body. If your goal is to have a true sissygasm, with no clitty stroking, then you can! Just keep doing what you are doing, listening to your body, and you will absolutely feel yourself approaching orgasm. If concentrating solely on your p-spot isn’t necessary, I highly recommend deeper insertion. You can turn up the vibrations as you go deeper. My favorite thing to have you do is sit on the edge of the bed, feet planted firmly on the floor, and ride that toy into bliss. Grind against it, feeling it fuck you just as deeply as I would!
Ideally, you are not playing with your clitty- you are retraining your body on how to have an orgasm as a sissy. This may take a little time and patience, or it may happen immediately. Either way, it’s going to be a lot of fun playing, and when that explosion hits, it will be sublime! If you are having trouble with it, I’m here to guide you and advise you! You can give me a call, find me on Skype for a sexy testing session, or, if you need to be discreet in your communications, indulge in an email package! We will get you to your goal- a true orgasm as a sissy!
Check this out! Over at Sissyville, the lovely Ms. Harper wrote about some sissy masturbation techniques you may want to look into! Let us help you durinh a two Mistress call with your practice so you can accomplish your sissy goalsw!
Talk to you soon!
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Hello Ms Stephanie, just found your blog and thought I’d have a word on this although it’s from some time ago.
Now I’m on a feminine journey I only rub, grind or hump now.
Love pillow humping I use two pillows and straddle them and ride like a woman not only does the clitty rub but love the sensation of my inner thighs rubbing the pillow.
It’s strange when I started masturbating as a teen I would lay on the bed and grind it seemed the natural way to go. Only later did I start to stroke but now I’ve gone back to how I used to do it.
Marianne
Marianne- Thank you for stopping by! I adore helping people find the most organic way of pleasuring themselves, being as true to their nature as we can. Pillow humping is perfect! Do you use a specific fabric type for your pillow cases?
Thanks for the comment, I use a cotton one at the moment but might get a satin one for different sensations. I was on GG earlier is it many happy returns for today? 🎂
I’m a big fan of different textures to play with sensually, so do go for it! Thank you! Yes, Friday was the day!
Oh oh Ms Stephanie, i read the blog and i was so excited about it, I want to call you and Ms Erika soon
twirlllllllllllllllllll
sissy belinda! That would be such a fun call! Let’s make it happen!
Mmmmmm TY Ms Stephanie , That really makes me feel Awesome that you , complimented me on doing a good job !! It is truly how i feel sexually ,feels great doing the one finger thing makes me feel so feminine ,sometimes when really in the mood i like to insert my 4 inch fav slim plug, feels Amazing also !! xoxos
By the way Ms Stephanie, love this pic , Your hair looks Amazingly sexy !! xoxos
Thank you so much! It’s really rather versatile with just a little bit of time!
Wow Ms Stephanie, what an amazing post, ty so much , My fav technique is sitting in my recliner, usually with realistic dildo ,and hours of lite nipple touching ,n teasing ,finally i now use my one forefinger to rub the underside of clitty like im actually fingering my self, feels amazing ,heres the part where you might be mad at me, lol sorry , but i rub until just the point of explosion n then , i usually take 2 fingers n finish the job , Im sure i could just rub it n explode into my undies but i mainly do the 2 finger final stroke due to making a big mess everywhere lol !! thanks again !! xoxos
viola! Thanks for reading! I think you are doing a great job masturbating like a woman, and although I would prefer if you finished with just the one finger, sometimes it takes two fingers to push you over the edge! Try it with just the one and see how it feels, though. It may be better than you expect!
Will I actually be the first pet to respond? My gosh. All star Mistresses opining beforehand. Tee hee. Yourself, Mistress Harper and Mistress Erika
It’s time for full disclosure. I’ve yet to read your post. (Just the Title)
Much like the “underprepared” student I skipped to the answers in the key and found what I knew
Why? You noticed I didn’t ask “How come”?
We (I) don’t come.
I dribble.
Mistress Erika allows me my release through a caged jiggle.
Absolutely marvellous.
Stroking? Oh my, Ms Stephanie you must be aware by now, that my paltry p in my panties could scarcely be grasped…but now I should read. I realize I’ve gone against the grain and jumped (prematurely) to a a cumclusion.
Maybe a sissy can stroke!
But I doubt.
A little curveball. (True… reading now)
little peg- I love the fact that you just dribble. I’m glad you are reading it- it’s really not about stroking but I do like alliteration, and thought that using the word “stroking” would draw a sissies attention!
Hi Ms Stephanie❤️ Now that I have read your post (working on that premature commenting) I see that “stroking has been struck” from the options for sissy masturbation!
The elusive “sissygasm”… it is a special treat to be sure.
I have let it leak to several Mistresses that my lone sissygasm occurred while in the saddle of a Sybian!
Riding off into the sunset until Mistress…(yes it was a live session with a Dominatrix) pointed out what had dribbled out!
Up to that point I had never experienced this although I’d had a lot of playtime in the backyard!
(They don’t call me “peg” for nothin!). Well, they actually also call me peg for “nothin’ much” as well!🤏
Yes, I’m trying to achieve that again…(a sissy must have goals) and to that end I attempt this at every opportunity.
My purchase recently of a quite formidable thrusting vibrating butt plug is being put to good use!
Results may be forthcoming!
Mistress Erika’s little peanut is under her strict supervision and she will generously allow me access to it now and then.
My favourite (perhaps hers as well) is what I call my “Jiggle and Dribble”
While technically not touching my clitty but merely jiggling my little pink cage, I am able to achieve my permitted ruined orgasm….hence the “Dribble”
Is there a loophole here Ms Stephanie, that would qualify this technique as “sissy masturbation”?
(Ruined? Not on your life! I think RO’s are the bees knees!)
Thanks Ms Stephanie!
little peg- Indeed, stroking is not actually any part of a sissy girls life! I do love that you have had a sissygasm though! The “jiggle and dribble” method is something I may bring into play with one of my chastity pets soon. I’m glad you are enjoying your new toy! Keep us posted on the results you have!
You know that sissies shouldn’t stroke their little sissy stick, I do love making them hump away to their heart’s content. 😉 Pillows are a good thing for sissies to get used to riding.
I agree, stroking should be completely off the table at this point, so we definitely need to teach sissies to masturbate properly!
Oh, Ms. Stephane! When I saw the title I was like “What?!” Stroking and SISSY? An abomination! LOL 🤣😘
It’s true some sissy gurls “STILL STROKE” but to really, and truly, experience all you can as a female tossing that stroking aside!
I love love love these sissy gurl masturbation options!
Ok, girls, who out there is still “Stroking like a boy?” Humm?
How many of you have found the joy of diddling your clitty like a girl?
Ms. Erika, I completely agree- a sissy should masturbate like a woman! With the options I wrote about, or any that a reader may share, there is no reason “stroking” needs to be in a sissy girls vocabulary unless she is performing the service for someone else! Thanks for stopping by!
oh oh oh sissy rub rub rubby pat pat pat oooooh naughty
Hi sissy belinda! Very naughty but oh so fun!
Yes stroking is definitely off the table. When there’s is less than an inch left and no erection can happen. My go to method is to push it up inside and finger it like a woman diddling is what Mistress Erika calls it.
April- I love the sound of diddling! I’ll have to recommend it to my smaller sissy callers.
Hi !🤭
Not me
Me!
Mistress Erika…so many questions!🤭
I have. ?😜
Mistress Erika did you coin the phrase Diddling?