Only want to say that there does not have to be the air of humiliation involved. If that is a fantasy element you are interested in, it can be added later. First step is to get her to play with another guy first. Role play out in public together, pretend you don't know each other. Then involve others around you. Example, for us it normally starts at local or vacations area swingers club to have some drinks and we like to play pool. She goes to the pool table and puts some quarters up, if others are playing it she just finds her spot and racks up to play by herself when I come around and ask to challenge her.i sit across the room from her. We play and wait for others to join. In the mean time we play some dares out. When she loses at a game I have her remove her bra for a game, during which she will make a trip to the bar for a drink, make conversation with someone and "explain" to them she lost it playing strip pool with "some guy"! But she is going to play double or nothing next game. It does not take long to have other challengers approach and join in our game, unknowingly. Then she beats me gets clothes back and there at the table puts it back on. I then stay in the rotation of challenges or leave the area and watch from afar for a while. Have her play them for a piece of clothing. When she loses the first game she likes to walk over to opponents table and stand infront of him or her and slowly remove her panties, fold and place them on their table. Saying those are my favorites so she wants a rematch to win them back. During the second game, now "armed" and opponent knowing she is panty free she uses it to her advantage, "accidentally" opening her legs when he is shooting her direction, or bend over in front of him to flash him as she shoots. Then she has to decide what she is going to do next. Win and take them back and move on to find another tease, or lose and get creative or paying off her"debt" for losing and extra to get panties back too. Maybe take him out on dance floor and do some dirty dancing or take him for a walk back to "her" cabana for some time to "talking and touching". I can see and watch from across the room to make sure she is ok. We have safe words and hand signals defined ahead of time. I walk by every few minutes so she has the opportunity to say a safe word in her conversation for me to hear. She is allowed to go as far as she wishes. We have even left separately, we always have a hotel room nearby. Room is for us unless she decides to go back with new friend. If she goes without me I stay and enjoy myself for an hour or so. Our room I wire with cameras to watch her and guest without being there, she is safe. after going to the room she explains, that hubby will be arriving soon but I'm cool with everything. They normally recognize me when I arrive later as the other pool player. Then she can do as she wishes while I watch and film.
We have done this several times, not always successful but even if she does not find a friend to play with, we have a great night in our hotel room talking about the things that happened or could have happened.
Just the way we have found to break the ice and to ease into a night of play. She is always in control and knows that she only had to say a word and I'm going to be there, and that I'm always watching what is happening.