I’m (24M) a bit shy and body conscious about myself. I’ve only had casual sex with men before and I’m yet to do anything with women, though I really really want to.
It’s so overwhelming to the point I’d prefer at least 5-7 dates before I feel safe enough undressing for a woman. I’ve always wondered how people who fuck on the first date have the courage and confidence to do it. I envy that confidence they have.
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Make it a long date. Start with lunch, go for a walk. Go shopping, have dinner, hang out at a coffee shop. During this time, sneak in some touching and hand holding here and there. Talk a lot.
When things seem good, everyone is comfortable, go home and fuck.
I must have sexy felling from her before that. If the flirtation before the date is sexy then i woul go for it.
The confidence also comes when you realize the noble truth of sexuality. ‘They often want to fuck you, as much as you want to fuck them.’ Then proceed with clear confidence and mutual awkwardness.
I always let the woman lead in the first few dates. Which means more often than not it didn’t happen, but that’s ok. I think it shows respect.