So I've been post-op for a decade -- nearly all of my adult life. I started transitioning as a teenager. I was one of the youngest patients ever of Dr. Meltzer at the time of my surgery. I had also been with my spouse -- a woman who I started dating right before I came out as trans, and who had fully accepted me -- until late last year. After the fourth time of being cheated on, and nearly daily being targeted for screaming and sometimes physical abuse, I finally ended it. We had already been planning to move to Iceland, and I have since moved there alone.
The culture in this country is... a bit different from the US. The prime minister is a lesbian. Same-sex marriage was passed by the Alþing (parliament) 59-0 (no votes against). The largest annual festival in the country is Reykjavík's pride fest, which is attended by 1/3rd if the country. Yes, there are homophobes and transphobes still (in fact, a recently-out FTM was roughed up in a men's room, making news a couple weeks ago) -- but problems are very rare. It's generally seen as very "uncool" to be LGBT-phobic.
Attitudes toward sex and dating are also very different. Dating... well, it's kind of a foreign concept in Iceland. If you meet someone and you like them, you hook up. If you hook up with the same person several times in a row without anyone else in-between, you're sort of de-facto together and then you might start going places together and cheating becomes frowned upon. But the default expectation with someone new you like is no-strings attached sex, not dating.
When I go out on the town at night, I'm *always* getting hit on, by really cute guys (Icelandic guys are usually soooo cute). I get too much attention, really, sometimes. I had one experience which... I've been calling it an "unwanted sexual experience", but I've had a couple other people tell me I really should call it rape, but I don't know. I did manage to keep him from doing everything he wanted to do to me. The experience kind of messed me up for a while concerning guys who are interested in me. But anyway, I'm still trying to figure out how to fit myself into the Icelandic dating scene.
In the US, I had always told myself -- no, promised myself -- that if for some reason I was ever single, I'd never sleep with a guy without telling him about my past. There was the trust in the relationship aspect, there was the personal-safety aspect, etc. In Iceland, however, this is proving very difficult, since people expect sex right away (the aforementioned guy who had trouble with the word "no"/"nei" seemed to think that because I had told him earlier that I thought he was really cute, that everything else was okay). There is no "relationship" to lose trust in; it's often *expected* that you hardly know the person you're sleeping with. And the society is -- at least in general -- much more LGBT-tolerant, reducing the safety-risk aspect.
So what I'm wondering is whether I should reconsider my previous assumptions about sex and disclosure. I'm currently overseas and this has been on my mind a lot.
One thing that's kind of constrained me so far also is fear of, what if I sleep with him and he can tell there's something different about me? Will he somehow know? And I really don't know that. I don't exactly have a long history with men. As mentioned, I've been with the same person, a woman, since I was a teenager. We had a couple joint trysts with one guy when I was post-op, but that's pretty much it. I really don't know... well... what it would be like for them and whether I'd have to face a situation where even if I might not be physically at risk, it could be emotionally taxing, having to explain my past in a moment of intimacy. But then again... I don't know. I just really don't know what to think about all of this. I've done "stuff" with a few guys who've been interested in me, but I've never gone all the way. And I think they just assume that since I'm from America, I have more prudish attitudes about sex or something. But I really don't want to become the "American Prude" here.

What do you all think?