Female led relationships discussion

Cobweb’s first year with his CB is coming up in a couple of weeks, and after the initial excitement wore off, daily life has taken over a bit; he now accepts his chastity as just part of normal routine. The constant attention I gave him at the start has faded slightly, which means his benefits have drifted too. He changed jobs after his directorship firm collapsed, among other things! I think he needs a relaunch, and I plan to use this first anniversary for that purpose, but I want something that will truly surprise and shock him. He enjoys cross-dressing, though it doesn’t excite me much—any other ideas are very welcome!