I have been training and owning sissies for 4 years now and 3 of my sissies have decided to transition as well. I have spent a great amount of time understanding and learning what goes inside the head of a sissy. From what got them started to what will push them over the edge.
Majority of the sissies start from wearing panties at all the different ages, some start early by wearing their mom’s or sisters and some start late by wearing their girlfriends or wives panties. But, Always remember panties might be the thing that started it all but bras are where masculinity is drained entirely. I have observed that oftentimes panties might be the thing that got them in but wearing a bra absolutely crushes any idea of masculinity that the sissy might have. Another one which is quite popular is the chastity cage, which is good but quite ineffective without proper sissification training(which includes hypnosis).
These things are more geared towards targeting her brain, thought process. When I am training my sissy, I prefer to train her in such a way that she develops a switch which can be turned on and off anytime by me. The sissy switch as I like to call it. A lot of the sissies that I train and won are married and have successful professional careers that they don’t want to be affected by them being a sissy so that is something which we can achieve using this switch and it also gives me one thing that I as a Dom crave, Total Ownership & Control. I have used this switch at times to torture my sissy through cum denial by not letting her fuck her wife on their wedding anniversary or by making her go shopping physically in boy-mode at Victoria secret.
By making a sissy do this and some more, you slowly transition her mind to function in such a way that the boundaries that masculinity would often prevent her from doing will no longer be there and once that happens you have now a perfectly submissive trained sissy in your hands that you can use for your pleasure in any way you desire.
I hope you liked this. If you have any questions, feel free to ask. I would love to answer any and every question you might have.