I believe you should let her "date" on her terms. Just give her permission and encourage her to explore. That way she isn't feeling pressure with you being present and she can explore and play on her terms. A separate dating life is essential for me.
In your situation I also recommend a QUALITY lifestyle meeting site in order to find compatible others. A "lifestyle club" might be a bit too much because many of them are kind of seedy, but, you could find one and sit back and observe. You could also chat with others who approach you and she could become accustomed to it, especially the girls. If you have the financial resources, you might attend a "non-lifestyle" resort such as a nudist resort, but one that is classy. That way you would be around sexy people and nudity with others would be a bit "normalized" for you. Hidden Beach in Cancun Mexico, Secrets (topless but sexy) and a few others would be VERY sexy and fun for you, without the pressure for sex. Eventually you could advance to Desire Resorts in Cancun (couples only) for lifestyle play if you wish. We have been to Desire RM a few times but honestly, as active as we are in the LS, we have never actually PLAYED there. We just hang out, have sexy fun and if the RIGHT COUPLE or single is found, we would play. We suggest the Bliss Cruise, where there are thousands of lifestyle couples and you can be fully clothed, topless or fully nude if you desire. Tons of hot people and tons of opportunities to play if you want, but no pressure to do so and we believe that many of the attendees don't play at all, but are there for the sexy environment. If you are both on the same page but a bit confused and unsure how to continue, then just have some fun, nude recreation as described above.
Mrs Hotwife