Nervous about having sex after a long time, quite inexperienced ;/

Hey all,

Well the title pretty much sums it up - I haven't had sex in 2 years, and I've never really had a 'proper' relationship with another guy. I've also only slept with one guy and I'm 24. I'm very insecure and shy, and have passed many opportunities to have sex (FWB kind of things) when I so desperately wanted to (I'm pretty sexualised with my humour etc and I talk about it a lot. I also do not reject offers for any kind of religious reasons/not having sex before marriage, I just hate it when my moral compass kicks in and think to myself I may regret it).

Anyway, I've been talking to a guy for quite sometime, met in person and all of that, we get on great. We are going for a night out this coming weekend, and because he is a train ride away and would have to leave early to get the last train, I said he could stay at mine. Anyway, our conversations are very tongue in cheek, we have talked about sexual things (again, I talk about it quite a bit, I'm very open minded). He is very similar to me - he is a couple of years older yet never has had a proper girlfriend and only had sex twice (there was me shocked because he's really handsome and very desirable to my eyes at least, but again he is shy).

I'm just really nervous because I know it is inevitable we will have sex (or at least I hope going by our conversations - btw I don't mean like sex talk, just jokey innocent kind of comments), and I'm kind of happy with that since I get on with him. I just have visions in my head, which do make me giggle, of me sitting there all shy, and he will also be shy, so I may have to pluck up the courage and make the first move (the thought terrifies me lol).

Any ideas on how I can approach it? I'm just scared that he may get back to mine, not seem so forthcoming (maybe because he is shy) and instantly the negative part of me will think he doesn't want to and that he doesn't like me as much. I really don't know how to read guys most guys would be very forward, and I'll be so worried that he doesn't like me or that he doesn't want sex. For instance, I dated a guy about 6 months ago (we've been friends for a number of years), again we talked of having sex. Anyway, I stayed over at his, and nothing happened. I felt so down because we talked about doing all of these things, but it never happened. I instantly assumed he found me repulsive (harsh word, however we still talk and we are friends and everything is the same, he said that he wasn't feeling very well which in retrospect may be feasible). So any negative vibe I get from this guy will automatically get me down in the dumps. Any tips? (and of the 'advice' variety ).