I honestly think that’s the biggest obstacle. I’m just not quite sure how to get there. I’d love an arrangement like yours.
I'm sure I have said this elsewhere but I'll sum up our journey.
1. We watched porn together and had an enjoyable sex life
2. We went to a nudist resort for an hour just to see if she would like it. The one we went to is an adults only place that has a good number of swingers.
3. We went to a swinger hotel that allows nudity and hung around with swingers and nudists.
4. As can be expected swingers approached her (not me) and asked if we would like to join them and we cautiously did. They were very kind and patient for her sake. That was the first step towards building trust. She learned that I was not jealous or critical of anything she did.
5. We started seeing other couples on occasion as soft swap swingers.
6. She led the way to full swap. Give a horny lady a glass of wine and no consequences and get out of the way. if you get to this point you have to realize that her sex drive may be far more than your own. You need to make sure you don't have any hang ups.
7. Then I suggested we set up an account on an adult web site for her and let her talk to men. By then she already knew I was OK with it. She got lots of attention.
More men than she could possibly meet responded. All that male attention was an aphrodisiac. By then she was accustomed to the idea that she could flirt and have sex and I was going to be happy about it.
She is in her 50s and her lovers have ranged from 25 to 70. She still has a preference for men in the 40 through 60 range but the young ones who want to come back for more really make her feel sexy and desirable.