Men that crossdress and also enjoy humiliation and potentially BDSM can often find themselves becoming Sissy Trannies, where they can then adopt hyper-stereotypical female attributes as part of their sissification and feminisation. More often than not the sissy's partner (male or female) is the mistress and the sissy is ultra-submissive.
There are varying degrees of being involved in the sissy world, some men just like to dress up in very frilly pretty dresses and panties while other aspire to be the best sissy maid they can be and their training can also involve male chastity devices and other bondage equipment. A proper sissy will of course do the household chores and be at the beck and call of their mistress at all times for whatever level of humiliation is the order of the day!
As well as the term Sissy, other fetishes that fall into the same realms include petticoating, cuckoldry, forced feminisation, emasculation infantilism (adult babies), and erotic humiliation.
Traditional sissy maids outfits and princess dresses are not what most would call sexy, they have a very childish look to them made predominantly from satin materials with lots & lots of frills and ruffles covering all of the upper body, with a high neck, and coming to at least mid-thigh if not longer. Many of the actual maids uniforms are black with white apron and under-skirt but the other dresses tend to be very colourful in very girly pinks, purples and blues.
The ruffles of the petticoat can be hiding such things as butt plugs and chastity devices used to control the sissy. Very often the mistress will be adept at giving the sissy maid punishment with a strap-on, also called pegging. The sissy world tends to be more fetish & extreme in nature than a lot of trannies and crossdressers undertake.
There are lots of professional mistresses that will conduct sissy training and the sissy is made to perform a range of mundane household tasks that a real maid would perform and also degrading tasks that invoke erotic humiliation. The sissy maid might also be instructed to perform sexual acts on their mistress or others, placing the sissy in a submissive/passive bdsm role.