Hi,

If you are interested in certain things, so long as you are a gentleman, it does not hurt to ask.   Of course, realize that the lady has the prerogative to say no, and if that happens, move on, have a good time and don't fret about it.    

Read it.  A lot of providers are happy to help you with a fetish or fantasy and advertise that fact.  I post my skills on my site and note "if it's not listed here, I probably don't do it."  I had a new client ask me for Greek once prior to and three times during a meeting when my site and I told him it wasn't on the menu.  He's not welcome back.

..break out!

I love to try new and different things.  I enjoy expanding my horizons.  The only thing I don't like is anything in or near MY ass and I won't tongue your ass.  But, most anything else is cool with me.

I think you are asking about simple things. It isn't like a serious kink scenario plan.  

for example, to take the case of the OP.

You might want to start massaging, then kissing the feet.  If she draws back from that, then it's time to head in another direction.  You need to be able to read the gal's body language, and keeping an eye on her facial expression is also a must.  If she winces at something, back off.  If she smiles then that's a green light.

Like any important art form, sex takes practice and practice makes perfect.

Till then, stick to the bunny slopes.

Recently I was with a friend who I have seen many times and we are totally relaxed with each other.  We often try variations (positions, dress, etc) and I asked her if she was interested in trying something neither of us had done together before.  She said, "no I don't like that," so I assume she had tried it and didn't like it, although it would have been a new, but not radical experience for me.  So I left it and we went on about our business which, at least for me, was intense.  Don't let the search for perfection be the enemy of the merely transcendental!

others have had CIM or COF or whatever you desire, then your chances of getting a "sure baby" reply are good.

I personally love a pre-playdate email along the lines of "Hey, X, Y, and Z are things I really enjoy, and I was thinking about trying such-and-such if that sounds fun to you".  It's an un-awkward way for you to ask for what you want, and an equally un-awkward opportunity for me to say "no thanks" to anything I don't feel comfortable with.  In short, it allows us to un-awkwardly jump right into your favorite fun stuff when we meet!

It should go without saying that activities like Greek require advance preparation, and should therefore be discussed...in advance.  

Asking up front before things get hot and heavy, so that you don't have to take a time out mid-stroke to ask and potentially be let down.

...a newbie and/or a monger you have never met?

In fact, in addition to references, I ask for at least little info about his interests.  I want to make sure that I am the right lady for the job!

receive radio silence from me. For me, it is never ok to discuss anything sexual whatsoever via email. Even if I've screened someone, I will cease communication if he sent any sexual requests.

...I PM wasn't possible I wouldn't discuss that stuff until in her presence.

There is a difference between kissing someone's feet, trying to suck on one of their toes, kissing the neck, grabbing the ass etc., I also don't think you ask those things, you let it evolve, you go for it and see what happens.      However, when it comes to something like CIM, unless you know it is standard procedure, I would not suggest that someone just go for it, the rest of the session, if there is any at all, may not be too enjoyable if that is something that is not on the menu.  Of course, if a person does his/her research, he/she should have a good idea of what is available (PC nod to Lopaw).

I was trying to make. Go slow, build up and pay attention to everything - verbal and non-verbal. Obviously, if the body language clues are ambiguous, you gotta use words to clarify. I don't advocate being "pushy", especially since theoretically we know her general boundaries when going into the date. I suppose we all started on the bunny slopes at some time!

especially about the Greek. I don't want to push anyone's boundaries and was responding from my own level of comfort - not responding directly to newbie anxieties. I am presuming that I already have some understanding of your boundaries from your profile and reviews before we even meet.