Open menu

Breaking Sissies @sissybreaking

30 Images
NSFW. A blog full of pictures of sissies who have either been totally forced into submission or are on their way. And some hypno. - Breaking Sissies (@sissybreaking)
Theblackmaster55 makemeyoursissygirl this is @sissybreaking



this is fucking perfect

Bitch breaking!

The first seconds of her new life as a true sissy cumslut. The detail in this image is amazing. The running mascara, streaked by her tears, the ball gag, the worship of her new daddy in her eyes. And of course, the sissy cummies that squirted straight onto the wall.

She had never cum that much or that hard as a man, and now she’ll never have he chance to try again. :D

Ppsperv i cant decide whether i want to be @sissybreaking


I can’t decide whether I want to be that sissy or licking His hot Black hole!

Follow my tumblr—> Pretty Pink Sissy Perv

I want this so bad!

Ppsperv follow my tumblr pretty pink sissy @sissybreaking


Follow my tumblr—> Pretty Pink Sissy Perv



like he owns you. The operative phrase.

Enjoy your Fate #BlackNewWorldOrder

Ppsperv follow my tumblr pretty pink sissy @sissybreaking


Follow my tumblr—> Pretty Pink Sissy Perv


Invite him to enter you. Arch your back. You belong to him.

So hawwwwwt really need to find a skirt like @sissybreaking

So hawwwwwt. Really need to find a skirt like number three. :D

So heres our starting point i figure my first @sissybreaking

So, here’s our starting point. I figure my first short-term goal is to get smooth and hairless, and in the longer term I need to lose some weight.


Next week we’ll hopefully have some better, hairless pics.

Bigblacksissybanger thats what i define as a @sissybreaking


that’s what I define as a perfect date, though I’d replace that tail with something else….me.

Holy shit yes please!

Blackbeastandboibitches there is no known cure @sissybreaking


There is no known cure for being a bitch for black dick. It’s permanent. There’s not 12 step program, no way to wean yourself off onto less faggoty cock love. Once you’ve tasted it you’re hooked for good. That’s why so many white bois who thought they were “straight” or “bi” or “curious” have turned out into nothing but whores waiting for their next mouthful of dark chocolate meat. They should never have slobbered over their first black cock if they weren’t ready to keep at it!

So hot!

Sissyalicelovesbbc yesi do another broken @sissybreaking


Yes…I do.

Another broken boi!

Machine training of course judging from her @sissybreaking

Machine training, of course. Judging from her eyes, I’ll bet her stiff little clitty is already leaking.

Sissysissysissysissysissy its so much easier @sissybreaking


It’s so much easier when sissies just give in like they should. Much less fun though.

Another great training method is to put a bunch of @sissybreaking

Another great training method is to put a bunch of sissies in a room together and let them go at it. As the more dominant ones pound the weaker sissies, both will begin to accept their fates. The bottoms, of course, will realize that even other sissies see them as nothing more than two more holes to fuck.

And the tops will being to associate the sissy form with pleasure and submission. It’s easy enough to turn that back on them.

And the last vestiges of manliness will drip out @sissybreaking

And the last vestiges of manliness will drip out of your asspussy.

Heres a sissy caving to her audiovisual therapy @sissybreaking

Here’s a sissy caving to her audiovisual therapy. After she’s tied down and the dildo is inserted, she’s bombarded with eight hours of sissy hypno, all of which builds towards an anal orgasm. When she has almost climaxed, we take the opportunity to introduce the really intense submissive material. Since they’re so focused on their clitty, it slips right in with zero resistance.

Look how excited that cock makes herbut even @sissybreaking

Look how excited that cock makes her.But even though she’s leaking, her hand is still on her hip like a good sissy. So well trained. :D

Sissyalicelovesbbc i cant wait for my first @sissybreaking


I can’t wait for my first “forced” sissygasm…trying to resist it and having it wash over you all the same…

The first sissygasm is, as y'all might have guessed, the most important part of the process. Although only a rare few sissies break outright, it sets most down a path they can’t turn back from.

Although its rare there are times when letting a @sissybreaking

Although it’s rare, there are times when letting a sissy cum all on her own can be a useful tool. Jocelyn had been resisting her therapy for weeks, including tons of pussy pounding and cum swallowing. So we unlocked her, gave her a dildo, and let her connect the dots herself.

Look at that happy sissy face!

Sissysissysissysissysissy i dont have anything @sissybreaking


I don’t have anything for this. It’s just super hot.

Iamgraciegirl hmmmm again no cock cage on our @sissybreaking


hmmmm again no cock cage on our sissy but at least she will always equate cumming with having her sissyhole filled and pounded hard…….. she will now need…. NEED to be fucked to be able to cum…… 

Yes indeed! The proper way to train a rebellious whiteboi.

I need cock daily thats almost heavenly a @sissybreaking


That’s almost heavenly!

A hands-free anal orgasm. A true sissygasm.

Secretfemboi so hot for the ones with a @sissybreaking


So hot :)

For the ones with a little more mental fortitude, it’s often best to combine a full-on ass pounding with clitty stimulation. Rubbing right below the boi’s little mushroom can often send them over the edge in true sissy fashion, each release moving their minds closer and closer to the inevitable, mewling, moaning, dripping, sissygasm.

Tsuchiro this story is sending chills down my @sissybreaking


This story is sending chills down my spine. This is what I want.

She’s the ideal. The perfect one. The final product. Every sissy is broken in with this total submission in mind.

Totally broken now just desperate for the only @sissybreaking

Totally broken. Now just desperate for the only release she knows.

This is what happens to the weaker usually @sissybreaking

This is what happens to the weaker, usually whiteboi sissies. The hypnosis starts in and they  immediately cave, beginning to fuck themselves silly with dildoes and wear buttplugs when they can’t. Once they have their first sissygasm from anal only, they’ll be bitches for life.

Hypnosis is a key ingredient when it comes to @sissybreaking

Hypnosis is a key ingredient when it comes to breaking sissybois, Here is a simple one, best used inbetween lengthier, more powerful sessions.

Ill bet your little dicklet is running like a @sissybreaking

I’ll bet your little dicklet is running like a faucet. Some man you were, and now you’re just a broken little whiteboi, begging for a hot sticky cumload deep in your boipussy,

Look at how hairless and round that ass is if he @sissybreaking

Look at how hairless and round that ass is. If he was anything close to a man before he was bitched by that bull’s cum, she’s certainly a sissyboi now.

Old school sissy breaking but running on train on @sissybreaking

Old-school sissy breaking. But running on train on “her” newly sissified white ass is certainly effective, and will make her a BBC-craving cumslut for the rest of her life.

Her hand on her clitty is just helping the process along.

Look at her mouth shes almost there she knows @sissybreaking

Look at her mouth.

She’s almost there.

She knows the last of her masculinity is about to come dribbling out of her new clitty,

Sissysissysissysissysissy here we have an @sissybreaking


Here we have an almost completely broken sissy. Notice the general lack of body hair, small clitty, and lean body that signal her complete feminization, as well as a lack of restraints, no doubt thanks to hypnosis and dildo training. 

Now we just wait until she gives in to the pounding and her building sissygasm.

You've reached the last post... but there's plenty more to explore!

Search for: sissybreaking
View profiles recently viewed by others