I have had a relationship with another married middle aged man for several years. Our activities consists mostly of mutual oral sex and rimming. After our last session he mentioned that he would like to try anal sex in the future with him being the top. I have wanted to try but we both are so conservative sexually I was reluctant to being it up for fear it would screw up an epic FWB relationship. I did mention once that I enjoyed wearing thigh high stocking as a turn-on and he was sort of indifferent. Seeing how he brought up the prospects of trying something new in our relationship should I tell him about my desire to be with him while wearing lingerie or just surprise him the next time we get together.