maybe suggest something alone the lines of wearing panties or something like that and see how she reacts? What do you all think would that work?
I liked Sara's idea. One day, pick up a pair of her panties, tell her how you think they would feel much better that yours, and ask her if you can try them on. It might be a great start.
The crossdressing community is one that needs to stick together and continue to be there for each other for whatever one needs. We are always trying to improve the forum to better serve the crossdresser in all of us.