My wife and I will be spending a couple days in Chicago in February. While I have been partaking in the hobby a few years without my wife’s knowledge, I would like her to experience it as well with an erotic massage from a male provider. She is getting more sexually adventurous as she gets older but I highly doubt she would agree to a planned encounter if I asked her to do it so I would like to just surprise her with it. I’m fairly certain she would do it if it was more spontaneous for her. My thought was to have a male provider show up to our room when I have stepped out. My plan would be to meet him in the hotel lobby, pay him and then have him go knock on our hotel room door. When she answers I would have him give her a note I have written telling her that I have hired this massage therapist as a gift for to her and she should just lay back, relax and enjoy what he has to offer. I think she would thoroughly enjoy an erotic massage and possibly being eaten out but I don’t think she would “go all the way”.    
My question is, have any of you men done this for your wife, or have any of you women done this for yourself and how do I find someone to provide this experience?  Or if you have any suggestions on how to present this to my wife, they would be welcome. I would insist that the provider of this service be someone that is very good looking, respectful of her boundaries and experienced in this area. Thanks in advance for any help.

I would be VERY reluctant though to surprise anyone with an intimate encounter.  First, ask yourself if this is truly for her, or if its really for you? (Example, I frequently buy providers outfits.  But, they are always for my benefit).  If you can't discuss this with her in advance, and get some sign off, then maybe its too soon.  Also, if you don't clearly communicate what you are prepared to allow, and not, then you should be prepared for everything to occur.

 
The most I would risk would be to tell her that you hired a masseuse for both of you.  And, once he arrives to the room, let her know that he's a specially skilled masseuse, that he's going to massage her first and that you're going to step out of the room.  At that point, you can let her know that you're okay if she wants him to go beyond the standard massage.