We all know that sissies don’t exactly stroke their cocks like a man, so why in the world would I be writing about sissy masturbation techniques for Stroketember?! Because sissy stroking doesn’t have to look like what an alpha male does when he’s busy jerking off. Silly sissies get caught up in the masculinity trap all the time, and wind up thinking they have to act like a man when they’re incredibly ill-equipped to even shine the shoes of a real man. Instead, I have some tips and techniques for all sissies to really bring your sissy-gasm game to new heights. Keep on reading for five badass techniques meant to make all sissies cream their panties.
Five Sissy Masturbation Techniques
Sissies have been coming up with interesting ways to tickle their clitties and make their eyes roll back forever, but I bet I can bring you at least a couple of ideas that are new to your masturbation game. Use these one at a time or all together to really reduce your brain to a slimy liquid. We start at the top, with Nipple Teasing.
Tease those nipples, sissy!
Not all sissies have taken the time to cultivate the needed sensitivity to nipple play to be able to completely orgasm just from a little light nipple teasing, but some have! If you have, you’re going to love this, and if you haven’t taken that time yet, you’re about to. Mistress Harper’s patented sissy nipple teasing technique involves you using just the very tip of your finger to tease across your nipples, barely touching. Make sure there’s nothing between your nips and your teasing fingertips, and keep going until you can’t take it anymore. The key is a very light touch, just enough to be touching but not firm rubbing (and just imagine how good that touch would feel for some cock teasing!) Enjoy!
Have you tried… a pillow?
Pillow humping for sissies is a tried and true technique and if you haven’t given it a try yet, you should! You can either lay on your side, tuck a pillow between your knees, and do some side crunches to bring that pillow into contact with your little sissy clitty, or you can fold a pillow in half and kneel over it, as if you were riding a nice big cock cowgirl style. Either way works well to really help emasculate a sissy! Try humping a pillow next time you’re in the mood for some sissy masturbation.
Anal-gasms are the best sort of sissy-gasm you can have!
For sissy masturbation, nothing beats your standard dildo in the ass routine. I’ll leave it up to you exactly how you manage to get that gorgeous cock into your sweet sissy pussy (bussy, if you will), but my personal favorite is to use a suction-cup base dildo and have you back that ass up onto it. Remember if you’re using your toy in the shower, to invest in water safe lube, and to keep your hands off your sissy nubbin’. Your goal should be to orgasm just from being filled and feeling that delightful friction in your ass.
For sissies who want to lose their minds, try toys.
Coming strongly recommended from a long time client of ours, try using a clitoral stimulator style vibrator on your sissy clitty. There are a couple of different styles you can choose from, ranging from stimulators that create suction by rapidly moving a diaphragm back and forth, to sonic vibrators that use sound waves to pulse over a very specific spot. Try the Lelo Sila – Cruise and let me know how it worked for you. I’m willing to bet you’ll love it the way I love it.
Final sissy masturbation technique: rattle the cage.
For this one to work, you need some equipment, sissy. Start with a chastity cage, and add a strong vibrator like the Magic Wand. Just like the pillow humping technique, you’re going to have to do a little work. Lay your vibrator on the bed, and then hump it. Bring your chastity cage into contact with the vibrator so that it causes the entire cage to transmit vibration to your locked sissy swizzle. You can combine this with some anal play, maybe toss in a vibrating butt plug to really make your brain explode.
Are you ready to try some sissy masturbation?
Of course you are, sissy! Everyone knows sissies can’t keep their hands off their dicks, that’s why one of our favorite months is coming up soon. We may be in Stroketember now, but Locktober and No-Nut November is coming up fast. Better get all your sissy-gasms and cute wittle orgasms out now, because we’re gonna be exploring sissy chastity next month. That last technique is going to come in really handy for all the sissies really soon. Better bookmark this page just in case, sissy.
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Want more Sissy Masturbation fun? Ms Stephanie has some advice for you, too! You should hit us both us up for a two Mistress Sissy Humping fun.
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You know, pillow humping (especially) *does* count as stroking, doesn’t it?
I love the suggestions you’ve left for Our little sissy gurls, Mistress Harper! Few things make a gurl feel more girly than masturbating like one!
Speaking of which, I’d been waiting for someone to say if they’d used a clitoral stimulator on their sissy clitty, and if so, what were the results? Even if it’s not as all-encompassing a sensation as other methods, I just know the euphoria from using the same thing You use on your pretty pussy to come to orgasm will vault these gurls into squirties!
Can’t wait to hear what the gurls try, and all about the giggly, tingly, panty-goo-ing results!
I figure anything that rubs back and forth on their wee sissy clittys counts as stroking! even the super fast ‘rub’ of a vibrator.
The clitoral stimulators, I actually heard from one the sissies of the Empire that they work ‘really’ well, as in ‘amazingly mind blowing-ly well!’ Have you met Paisley? She has one, and it makes her sissy eyeballs roll back. rofl
I know for a fact there are quite a few pillow humping sissies, but did you also know there are inflatable fetishist/sissies that like humping pool floaties? What say you, sissies? Would you hump an inflatable for our amusement?
OOoooh, pool floaties?! That would conflate a lot of different interests, from inflation to vinyl, plus some humiliation.
Of course now I want to use an inflatable sex doll as a pool float.
Tapping a metal cage with a spoon until the clitty finally dribbles out. No reason to ever take the cage off.
That would be fun too; very similar to using a vibe on a cage, only slower and more agonizingly teasing. I think I like this idea!
Everything you just mentioned happens to be on my list of favorite sissy masturbation torment techniques. I do love when they get all squirmy and start begging for release! I wonder how many sissies are reading this and humping a pillow right now?
Any sissies being naughty and abusing their bedding should call us, so we can share in the fun! It’s always more fun to do your dirty sissy games with an audience, after all… We should team up and make some sissy’s day!
I have used two of those techniques—pillow humping and a vibrating egg.
I don’t know how common this is, but my nipples simply do not result in any erotic stimulation no matter what I try.
A pillow works well, but a vibrating egg is incredible! However I have to keep it on the very lowest setting.
I’ve never tried the anal-gasm technique, nor rattling the cage.
I’m kind of hesitant to try the anal-gasm technique, someday I’ll get over the hesitation, maybe after some inhibition reducing alcohol…