Make Me Your Sissy Bitch!
If you visit D/s sites or have one yourself these guys are all too common.
They want to be a “true” slave to a woman. Any woman, say, DommeBot Model X17-R.
Female Supremacy: Men are the Slave Property of Women
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That is any woman who will create the man’s fantasy down to the last jot and tittle.
For some reason these guys generally crave two things: hardcore orgasm denial (often never being allowed to have an orgasm ever) and sissyfication. After all what could be more degrading than being forced to resemble a female?
Their attention to detail can be staggering. I recall one fellow who knew exactly what color of dress she’d “make” him wear but also the direction from which the air current would cause the skirt to rustle.
Tom has a good post on the Do/me subs of the Land of Chastity:
I confess that after seeing this for several years, I’m still amazed that men write to these web groups professing their indiscriminating desire for a woman - apparently any woman - who will keep them permanently “locked up (the vernacular in the Chastity community for being kept in a device), and “forced” to dress in women’s clothes, to be a “sissy maid”, to have them take other lovers, and to be humiliated in dozens of other ways that would surely end a more “normal” relationship in a New York minute. Generally I avoid comment - there’s an unspoken rule in the kink world that one does not jump all over another person’s kink, no matter how distasteful it may be to you.