Chastity and orgasm denial discussion

A quick recap on my unique situation. A good friend, S_, is my key-holder, no play between us outside of the game, when she wants to release me she gives me the keys and I take care of the rest. She really doesn’t care what I do as long as I don’t cheat, or do anything too stupid(don’t ask, but it’s cost me). I also have a head-turning lesbian I “date” from time to time. Which works out great, because I do enjoy company when I dine occasionally, and with her I don’t have to worry about having to explain my situation. Now for my predicament: Saturday, I was at a pub that I frequent for lunch. The bartender was a you lady whom I’d made a pass at a couple of months ago(yes, I was locked at the time). She shot me down, as I expected. Most of the time I flirt with women and hit on them it’s for sport, at least that’s what I tell myself to pretend I don’t mind getting shot down. Back to the point, this lass asked me out. At least that’s the way I read it. She had a specific idea, and I told her we could do that. She’s got to figure out when her work and school schedules allow it. Thinks are a bit messed up here right now thanks to a little wind storm we had a little over a week ago(it might have made the news, not sure). Anyway, I know that IF we hit it off, and I wish to pursue something with her, that S_ is going to want to meet her before I get the keys. S_ has known me for years and has seen me make one tow many mistakes with my choice in women. Sure I could cut the device off, but that would violate the trust that S_ and I have, so I have no choice. The predicament is this, IF things go that direction, exactly how do I explain all this to the lass who asked me out? Something tells me, my usual bluntness might not be the best way. Course, it may not even come close to being an issue. Yeah, things would be a lot easier if I had a more conventional relation with my keyholder. It’s time for me to go find Morpheous, Hoss