We have been talking and roleplaying the idea of her with another man for over two years. She was fully against it at first but over the last few months she has really warmed up to it, even explicitly saying that she would do it with a specific person.

We have twice made plans for a specific time that we would both go to a public place to have her meet and leave with another man. Both times, the mood was soured when she suddenly got her period early, just before the date. This could be a huge factor in why she did not proceed, but I cannot say for certain.

The first was a hotel and the idea was to have her go to the hotel bar to get hit on by a stranger. We didn’t find any patrons that she was interested but she did flirt with our server. Later she told me to go find him and see it he wanted to come to the room, but she backed out before I could find him.

The second was an event where we expected to see people that we knew were interested in her for awhile. The idea was that I would leave early and she would stay and leave with one of them. It would be the perfect cover because he would just be giving her a ride home. This was last night. She said that she definitely flirted and danced after I left but she ultimately called me to come pick her up instead of proceeding with what we had planned.

Both of these times were over the last month, and we have had incredible sex while roleplaying what she “should have done”. Both times she took a much more dominant role, and had me playing a cuck role. She was really into it during sex so I know that the idea is in her head and she is enjoying. But I am not sure if I should strike again while the iron is hot or back off and let it settle.