Fascinating subject. I have a few. The first that comes to mind is having a session with two Mistresses. I knew one of the ladies, the other I met at the other Mistress' apartment the day of the session. Both were into the role play of "tarzan" being captured by Amazons. I didn't know which Mistress to focus on and the chemistry was off. It was like a little kid having too much ice cream.

Here's a funny one. I found out that body makeup is not a good idea. A Mistress I knew well had a private dungeon, she suggested I get body makeup that would match my leopard print loin cloth. (Again, it was Amazon / jungle type role play.) I bought makeup, did the best I could applying it and she had me crawling around her dungeon floor of hardwood and some carpeting. After a few minutes I noticed the floor was covered with my makeup. She said nothing and I apologized, ran to get cleaned up and came into the playroom to get dressed. She laughed, "What are you doing? Get the vacuum and clean the floors!" We continued the session after that and it was great.

Finally my longtime Mistress and I have done kink acts - not full sessions - at dawn on warm weather Sundays over the years in deserted public spaces (waterfront, parks, parking lots). I suggested GS and/or worshipping her strap on recently during moments of deep subspace. She didn't reject the suggestions. Aside from smartphones and security cameras, when I considered the logistics it wasn't worth the risk. My Mistress has talked trash about pimping me out when worshipping her strap on, but it is like your quote that it is "more fun to 'train' for forced-bi and keep the fantasy going."

Advice to subs, something I learned from experience, is when you come up with a session idea it is better to think with the head on your shoulders... and not the other one!