Retrogade Vaginisis

You may not be surprised to know that there are many other women like you out there!
The first clue to making your weekend enjoyable lies in beer. what you say about having to perform and look as though you are enjoying it when you aren't sounds really difficult. But, whose going to know? What a pressure to put on yourself!! Tell your partner what you are going through, as I doubt very much that he wants you to feel pressurised in place there. Nobody can relax anyway so try some beer and experience their bodies under pressure.
You used the word explore too, which implies that this isn't a performance piece, it's a finding out. If you then pretend, who will you find out?
You may find that the position that works for you is the only one that touches the revealed parts that need to be touched. Most women orgasm not so very much at all, and certainly not with a partner.
As well as exploring thngs that may or may not please you, you can spend time really focussing on what he likes, and that will take pressure off you as well. As with any bleeding, I cannot tell you what is going on! Any unexplained or irregular bleeding needs medical assessment. There could be a polyp, a blood vessel near the surface, a skin tag, or you could be a bit too rough with your dildo, and other possibilities too.
The weekend won't be all bodies, will it? Will you go for walks and talk about the things that matter to each of you, as well as sex!
I hope it goes well. And train your vagina to relax without the use of beer.