I'd wait until you know her very well and there is some trust built up.  

I've found that several times a gal was amenable to my fantasies.

It depends on the fantasy and how it is brought up.  

A client sharing thoughts during our downtime of things (such as roleplay or attire) that he has fantasized of gives me the chance to take the bait or not. I'm usually pretty receptive.

A client asking for a sex act he knows is not on my menu in the heat of the moment makes me feel put on the spot and awkward. I have menu Easter eggs, but those are typically given, not requested.

I am of the belief that you should be able to ask a provider for what you want. We are not your wives.
It is your Fantasy that you are purchasing and they're going to up the fee for the specialized service they are not comfortable with doing.

The thing is, providers are all different and hold different ideas of what a provider should do.
There are different levels to this Game.
If you have an Advanced Fantasy,  
     please seek out an Experienced Fantasy provider that can deliver the most memorable time.
The ones you have to "talk into it" are not going to meet and exceed the expectations of the Fantasy

I generally like affection, DATY, BBJ, cowgirl etc but there was time I was very heavy into BDSM as both a dom and a sub.  Every so often I get the old itch and I either find a provider who offers that or I go to one of my friends with benefits with whom the benefits were those activities.  

If I were  into it I would gladly ask a provider I knew to wear a cheer leaders sweater I provided, but that is very different from some of the other things one could ask which might make her very uncomfortble (The way I would feel if one of my patients asked me to take his/her appendix out.)  

 
 

-- Modified on 8/14/2016 6:44:18 AM

If she is someone who is familiar with you, you could try to approach it this way...

Tell her you'd like her opinion on how best to find someone to perform the services you want, and ask her if she knows anyone in the business who deals in the areas you are interested in...that gives her the option of volunteering herself or recommending someone else without feeling like she's been put on the spot...

Then it happened! Of course in true pussy fashion I sent my request via text. The fear of an awkward silence often gets the better of me. Much to my surprise, my seemingly vanilla viking wasn't so vanilla after all. Praise naked baby Jesus and let the good times roll.  

Thought for the day ~ Don't be a cunt bubble  nobody likes that shit 💥

Many providers advertise and do role play, but for most it falls. Into a limited list of options. Schoolgirl/teacher, secretary/boss, nurse/patient, a few others. So if you want something else, like seducing your brother's fiancée the night before their wedding, or a totally nonverbal session where neither of you speaks or "mimes," that's harder to find. Providers usually don't want to get into anything that involves that kind of work.

But some are not only up for it but really enjoy that kind of play. It has to be clarified what you want in advance, and that has to be done both with discretion and clarity. Or at the end of a session when you can set up the fantasy session.

But finding someone with that particular kind of skill is difficult.

worst that can happen is she says no. Providers are human too so we have fantasies too

Already know it then I'm sure you already know what she will say. It's not her job to make your fantasy come true if she doesn't offer it. It's her body and her comfort level. I suggest finding a provider that does offer what you want. I have clients that ask me if I'm into certain things and if I'm not I tell them. I don't care if it's a regular client or not. If it's not my thing and I'm not comfortable with it then I won't do it.

You never know how someone is going to react to a new idea. As long as you don't appear to be passive-aggressively trying to push it on her, there is nothing wrong with sharing it. Maybe she will be up for it. Maybe she will know someone else who she can refer you to? Gauge her reaction when you first start sharing to know when to stop, but by all means give it a try..

Just make sure she knows that you're just thinking out loud. If not, she might assume you are trying to make hints or suggestions... if it's something really far out of her comfort zone, that could be extremely intimidating to her.

An example would be if I were to say, 'Gosh, I've always imagined doing it in the middle of a crowded bar. For some reason that gets me going. But, of course it's just a fantasy... I'd never actually DO that, ha ha ha. It's really just the thought! I'm not even sure I'd be turned on if it were a real situation.'  

In that situation, I'd be saying it because it makes me feel good to talk about my fantasy... BUT I make it obvious that I am not trying to hint to my partner that we ever do such a thing.

Now take this example (happened a few weeks ago):  

Me: 'What's your favorite position?' (Thinking I was going to hear cowgirl, or mish, or some other usual answer)

Him: 'Well, actually, I really like Greek!!'

(Greek is off my menu except in rare cases)

I must have frozen, I don't even remember what I said. He just kind of laughed and said, 'Well, you did ask!'

Whether he was being rhetorical or not, it came across as extremely intimidating. That guy went from neutral to HELL NO!! NEVER AGAIN!! in as much time as it took him to say that.

-- Modified on 8/14/2016 11:44:00 AM

other than to agree with most of the great advices you're getting from the Ladies and Gents so far. It's up to you to make your choice and find out for yourself now, buddy.

I have a regular of mine that's been wanting a particular services for years and mentions it every now and again. Bottom line I'm not into it and I don't offer it. I have a wide variety of menu choices, there's always things to do to spice it up or go outside the realm. Will he get it someday? I hope, but not from me.

That being said, yes find another provider!