This may sound strange but when a guy asks what I'm going to be wearing it actually turns my stomach...
It doesn't bother me depending on which camp he belongs to. If a client has made a booking (meaning he's passed my security procedures so isn't a TW) then I answer his question with "it depends on what you'd like me to wear. Do you have any preferences?" But if he's just making an enquiry (and possibly just after wank fodder) I tend to say "That depends on what you like. If you make a booking I'm happy to take clothing requests". It's easier to ask them what they like than to go through the contents of my wardrobe for them anyway.
It disturbs me deeply when my clients tell me what to wear. I am always well dressed, wearing lingerie and high heels. Its a given. I don't like the tone they take with me, I feel like I'm being ordered around as some sort of put down. Maybe its imagined but I do think its sexist. I have never in my life told a man what to wear and accept them for who they are. Apparently, the feeling is not mutual.
Thing is you know "it's a given" but they don't, which is probably why they ask to be on the safe side, so try not to take it personally. Do you feel they are ordering you about or do you think they shouldn't even ask? I can understand if it's the former, but if it's the latter, as the customers, I do think they should be able to ask for specific clothes to be worn if they have a preference, assuming you don't say "clothing requests NOT taken" on your website. I'd feel a bit odd if a boyfriend asked me to wear specific items for a date (it's never happened though), but as a service provider I'd expect it. Men often have preferences and IMHO it's a shame if I wasn't dressed to their tastes, especially when you consider the sums of cash involved. Personally I feel sexier if I know I'm dressed to their tastes anyway, whether that's a business suit or jeans and t-shirt, so I prefer to know what they like.
Baffles me whenever I'm asked "Will you wear something nice?", or "Will you wear something sexy?"
Oh the fun I've had with men who ask these questions LOL. If they say "Will you wear something nice?" I often (if I think they can take a joke) say "Aw, I was hoping to wear something shit". Often when I'm told "wear whatever you like" I've said "great...boiler suit and wellies it is then!" ;-) Regarding "Will you wear something sexy?" I always ask them what their idea of sexy is and remind them that to one man it can mean the porn star look but to another it's more casual and understated. It's so open to interpretation as to be a completely useless question.
One client asked me to wear "whatever you wear when not working"...
I'm not sure what some men think I wear when I'm not working but if they knew the reality they wouldn't make that request, LOL. Waynetta Slob springs to mind!
My personal pet hate is when they ask, "are ya any good" grrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrr...
I hope one day someone will ask me that so I can say "no, I'm shit. I have no idea what I'm doing and I'm frigid too". All said jokingly of course. I can't imagine anyone asking and being genuine though.