What is the best way to ask for a specific style / kind of dress? I love high heels, but not strappy, sandal heels. I like the stilleto, closed, pointy or baby doll type...pumps.

Second, what about skirts, lingerie or garters and stockings?

I also have often wondered about long satin or velvet gloves. a glamourous, sexy look, but what is too much to ask for... Thanks!

I once had a gentleman ask for bright red or white FMPs.  He wanted 5 inch pumps, closed toe.  Honestly, this is something I would never have in my wardrobe and something I would have to buy, just for the appointment, and probably never use again.  I kindly explained this to him, and he asked my shoe size and purchased them.  I had another guy who wanted a particular brand and color of hosiery. Again, he brought them, when I told them they were not in my wardrobe.

Most ladies will try and accommodate a reasonable request.  The key is reasonable.  Many ladies do not have satin or velvet gloves.  In fact, finding these items may take a lot of looking at the more expensive department stores and cost $25 and up.  Not necessarily conducive to just one appointment.  If your preferences are that important to you, you may want to be prepared to go to the store after ascertaining their size requirements.  If your preferences are more general, most ladies are happy to oblige.  After all, the key is to "dress for success."

On a first date situation, I only ask for specific clothing items that appear in any pictures that the provider has on her web site or advertising sites. If the first date goes well, I will inquire if she has other items.