Long story short, I'm going to visit my girlfriend in the summer and we're going to be sharing a hotel room with one of our friends for an event. I've only ever traveled by plane once since officially starting my medical transition - to get top surgery. I had brought my Androgel in my checked luggage and it seemed alright, so I'll probably do the same again, only this time I'll just take what I'll need for that week and a little extra just in case something comes up. I didn't pack when going through security last time and my ID was all mismatched(male name, female gender etc, but it's fixed now), but I know I want to bring my STP(a peecock). Would it be best for me to just put it in my checked luggage and avoid the hassle of the body scanners and such?
I'm also thinking about the hotel arrangements. I trust my girlfriend, and our friend is another trans dude, but he doesn't know about me being trans. Since we're gonna be sharing the space for a week, I'm wondering if I should pack in my sleep/while chilling around the hotel. I tend to sleep in loose boxers without packing and I don't anticipate this friend coming close to touching me or staring at my crotch, but I'm a bit paranoid and really would prefer not to come out to him over something like this(read: I don't want to come out at all and value being stealth).
Any advice? Thanks in advance for your help!