Well I'm not sure when we will get the right opportunity, but cleanup is definitely something both me and her are very into. We actually almost had something lined up a few days ago, but it's a bit tricky finding the right person and having her in the right mood and having no responsibilities. I'm sure it will happen eventually. We did have one experience where she gave a friend of mine a bj and he went down on her, but sex never happened.
We took a slight break from the chastity, but I'm currently in the smallest bird locked they sell. It's actually very comfortable, unless it tries to get hard, but there's really not enough room to get very hard anyway so it gives up pretty quickly. There's really not enough room to even try to cheat in it and it's small enough that even if I managed to pull out of the back I really doubt I'd be able to get back in it. Ive only been back in it a couple days now, however she said I'll be in it for a month, but she'll let me out for 4 minutes each time she gets off from me going down on her... I think that might give me a pretty good chance after a few days. Last time we did something similar and she cuffed my hands behind my back before she let me out, so I imagine that's how we will do it. Last time I was in an older device that irritated right behind my head to the point where the skin was basically broken, so she felt bad and let me cum and then that's when we took a break from it, but I doubt I'll get a second more than the 4 minutes during this lockup and this device doesn't have the same issues as the other one. She's been pretty excited to get me back in a device, but we really wanted to make sure everything was healed up properly.