Enjoy peeking into my naughty mind to discover some inspirational ideas for exciting, humiliating, and erotic methods & fantasies of enforcing strict female authority

Sissy Bra Training

Train him how to wear a bra…making it like a (humiliating) lesson….like the first time a teenager girl wears one.   

Makes him practice taking several on and off in front of you.  Give him 5-10 things he needs to know about wearing a bra, and then makes him memorize them and repeat them back to you when you quiz him …(like, 1) never let the straps show, 2) always choose a color that doesn’t shine through, 3) always be sure the bra matches the panties, 4)….etc).   Make sure you quiz him when he least expects it, and give him a humiliating punishment if he should forget any of the rules you’ve instructed him with.   You could even get a girlfriend to quiz him for you, which would be absolutely humiliating!   

Insist that he wear a matching bra and panty set at least 2 days out of every week, all day, no matter what he's doing.  If we wants to be a sissy, treat him like a sissy and enforce him to wear these very basic feminine items. He should actually be wearing woman's panties every day, without exception.  

Pick 2 days out of the week (like Monday sand Wednesdays) and enforce the rule of having to wear a matching bra from the moment he wakes up, to the moment he's ready to go to bed.  Rub our hand over his back now and then to remind him you know he's wearing a bra, and also to check that he has it on.  It should be his responsibility to have it on always on those two days, and if you ever catch him without it you should enforce a swift and very strict punishment.  

You can punish him for not obeying by making him wear one 3 days in a row, extended chastity, not letting him wear shirts that will cover it up, or the best is to make him tan 3 times in a row with the bra on so that he'll have tan lines to remind him.   

The point is to show him you are willing and able to enforce him being a sissy more than he wanted.  By you over insisting and enforcing this, he's not only humiliated, but he's reminded on a regular basis of your feminine authority and his ridiculous status. You are teaching him a lesson to be careful what he wishes for.  

Have your girlfriends give him a surprise 20 second backrub to him when you he's wearing a bra under his shirt….   

Try to seek out any excuse to punish him and keep him alert when he least expects it.  Surprise him by opening his shirt, and asks him where’s his bra?.  Then explain to him how he will be punished, taking out a note pad and clearly noting the incident so that he sees you will not be forgetting about it later.    


  1. Hi,

    Great post. Speaking from experience, when i was first introdced to bras my femming really took off.

    sissy maid diane

  2. when i got my first bra it was a white lace with a little pink my female room mate got for me when as a joke i told her i wonder what i would look like in one well then why dont we found out she hand me a bra and hook it up it fit nice on me well i see you nice in that bra i think you should wear a bra all the time but you have to get your own just then she told me let go and buy you some bras and panties i was about to take the bra off when she said no she hand me a blouse and put it on now we can go once in the store she told the lady i need some bras and panties for my sissy she look at me well let see what size she is she open my blouse ans saw my pink bra i see you have her in one now yes and soon she will have other to wear after a year my breasts grow and now i look more girly and i become her house sissy

  3. My wife fully expects me to wear matching bra, panties, garter belt and hose when we go out now. I am to dress to impress her and this means making sure my body is smoothly shaved as well. I am not permitted to wear socks. If my hose show that is acceptable to her.

  4. I am made to wear a bra and panties while at home, my wife has bought me a platform bra complete with stick on breast forms with I must attach and wear with my bra. I have matching lacy panties and suspender belt with nude colour stockings which I have to wear all the time even to work. She has bought me barely black seamed stockings which she insists I wear around the house, she shaves me twice a week so I am kept a smooth sissy girl and my clitty is kept in a pink sheath which is held firmly between my legs so I have no naughty boy bulge in my panties. When my wife has her monthly I am forced to use my extra large tampons which she changes twice a day she always makes sure the little cord is pulled tightly under the elastic of my panty leg so every step I take I feel the pull on my tamponed bottom. Both of my sister in laws have seen me in my undies and have bought me matching bras and panties which my wife made me model for them, it was so humiliating especially when they saw my pink sheathed clitty.

  5. sexi room mates should put thier sissy in a bra and pinch their nipples