In case she decides to delete it:

So how would you want your boyfriend to tell you he was born a woman?

I want to make it clear that I usually tell people what I've got in my pants (or break it off) long before I get to this point. I had trouble fitting my screening questions into a normal conversation with this particular guy and one thing lead to another very quickly... now every time he gives me the once-over even I want to scream "IT'S A TRAP". So I already feel like a heartless liar and will not, as far as I can help it, be going this far with anyone again without having disclosed.

Personal info: I'm 25, trans male, on male hormones for 7 years, I've had my chest reconstructed, no surgical alterations done to my junk, but my parts are hormonally masculinised. I'm athletic, not girly, not gay sounding. You wouldn't pick me for gay, much less trans, so I'm sure my guy has zero clue.

I've known my guy for about 6 months and have been dating him for the past 4 or 5 weeks. We haven't done anything where I've taken my underwear off, but I've given him head a few times amongst other things... I think we'd both consider what we've been doing to be fucking. He started calling me his boyfriend at some point so I guess that's where it's at... He's 23, a total sweetheart, chatty, gay. I can't tell if he gossips or not, he's said a few things, but nothing that'd make me think he'd pass on something marked as 'secret' so far.

I wish it was as easy as, "psst, I'm a transsexual," but it's not. I work with him, and I need to know he appreciates confidentiality because I don't want my gender questioned at work. I got enough weird vibes after a female colleague outed me as gay to everyone in the building.

He's either going to be into it or not into it, that's probably already set and there's nothing I can really do to change his mind. My issue isn't convincing him that he really should want to bang me. What I need to do is break it off if he's a) Openly not into my kind of configuration and/or b) Might out me at work. It'd be an understatement for me to say that I'm into him, so I don't want to just break it off because I'm having trouble reading him.

My usual screening process is to bring up a number of topics and gauge my partner's response. Sometimes it's easy and right away a guy will let me know that he couldn't be into someone with a small cock|is super into the smallest of micro penises, or feels ill if female organs are brought up|is bisexual. My guy though, we always seem to have something to talk about and we never end up in 20 question land where I can hurl hypotheticals at him. I bring up small cocks and I get a "I don't think you have anything to worry about" with a subject change, and all I know about his opinion of female junk is that his older sister would have violent mood swings and send him out as a kid to steal tampons from his friend's mother's house. He has next to no knowledge about trans anything, so questioning him directly about if he considered trans guys to be guys ended up with a google search and a "I don't think she looks like a guy, or her, or her..."

I guess I've already decided I'm probably just going to tell him what's up, somehow, but I don't know what to expect. Well, that's not true, I'm kind of expecting a "I feel betrayed and lied to." That's how I'd feel. What I'm asking you guys is, if you were in his shoes, what could I do or say to soften the betrayal blow? Should I be apologetic about not having told him? Should I just let him take down my pants and act like I thought he already knew/it's not big deal? Should I invite him over and leave suspicious things around so he'll ask about them?

How would you want this kind of thing handled? How would you react? Would you be inclined to out someone as revenge?