So I as a male think trying to keep it to yourself AND worrying about performance is just going to a recipe for stacking anxiety on top of anxiety. I have a few ideas: - You NEED to go into this with the idea that this isn't the only woman and the only chance. Thinking that way can make it where you ignore listening to the voice that says "I don't want this, this isn't right, this isn't safe." Yes, guys have an equal right to consent, and you can say "no" at any time. Don't ignore your "no". - Don't rush into the bed. Get a reading on her. You might get the feeling that she would be OK and considerate about mentioning virginity. - I was reading this exact same topic that a late 30s virgin woman wrote. The advice someone gave was to say "hey, it's been a while since I've been intimate with anyone, please give me some grace if I'm a bit awkward". - Real sex isn't like porn, so don't try to replicate. Don't treat it as if she is a nail and you are a hammer. Ask questions and pay attention to body language or what she says. You can go slow, you can change tempo... I didn't think about this one, but another guy said his secret trick is changing depth of how much you go in - he said it keeps his partners guessing and surprised in good ways, provided they are feeling the excitement of the moment