QUESTION: She told me she’d never been physical with anyone. I’ve only been with women who were already pretty experienced. I really have no knowledge of what sex is like for women when they’re just first beginning to explore.
Basically, I want to know how to make this as easy, low-stress, and as much fun as possible. I want to know how much her first time is likely to be painful and how to minimize that. What misconceptions or fears she might have that I should address before we start.
RESPONSE: 1. Foreplay, foreplay, foreplay. You can’t do that enough.
Take it slow and let her guide you.
Block off an afternoon so neither of you feels rushed.
2. When the two of you start to get more physical with each other, see it as exploration rather than a destination in mind – and encourage her to do so as well.
Actually, this is probably even more of an issue for her than you. If she starts the day off thinking “we’re going to have sex today” that might make it hard for her to just relax and have a good time exploring.
So I’d just make sure she knows you’re happy to take a leisurely, exploratory pace if she wants to. But be ready with protection.
On the other hand, once she’s turned on she may just want to get down to it, in which case, have fun!
While it is important not to push her, she may be one of the many women who respond well to a certain level of aggression/assertion.
So if she seems to be looking to you to take the lead, don’t be afraid to do so, as long as you’re checking for consent and arousal.
3. Foreplay, yes. Relaxed, yes. Taking it slow, yes.
One thing to try is exploring her with your finger. Lick your finger first, and then playfully slide it into her vagina. This will ease her into the experience.
Ideally, you will bring her to orgasm, allow her time to recover and then start back up again. Penetration should happen right before her second orgasm.
She’ll be so turned on that she will put up with just about anything. You will meet up with resistance if her hymen is intact. Don’t attempt penetration unless you are fully erect. Anything less will be painful for her.