Starbuck, you've come to the right place to talk about what your boyfriend is up to...and, girlfriend, looks like you've got a few things to deal with...
First and foremost, of course, is: Is he seeing someone on the side in the City? While the condoms and sex toys MIGHT be innocent (he might be using the condoms to avoid soaking his clothes when he climaxes after getting himself off...MAYBE...), if he's "playing" with someone else, that's the most serious trust issue. Compared to that, just dressing in women's clothes is pretty mild. You really have to address that first...trouble is, I don't know of any good way to bring it up without dropping the "I know about your crossdressing" bomb on him as well.
Aside from that, the issue of him spending more money on his "girl clothes" when you're short of money as it is...that can also be a big deal. My fiancee gets on me if she thinks I'm spending too much money on Amy's wardrobe. And using your stuff without your permission is also in very poor taste...and can be downright unhygenic, in the case of things like makeup.
But him emailing photos of himself dressed to someone else...and taking all that clothing with him when he travels...and the condoms and sex toys...well, it doesn't take Richard Castle and Kate Beckett to figure out something's up. This is the time for one of those scenes where you tell him "We need to talk," in a serious voice.
Hopefully he'll recognize the jig is up, and come clean. What happens after that...is really up to you.
I hope you manage to pull through this, somehow. Know that, right now, my sympathies lie with you.
- Amy
