Ask Jenn – February 10, 2020

Hi Jenn,
What’s the best sex position for first time? And how can I reduce the pain of my female partner?

Oh…I’m so into this question!! Let’s get right into it!

First, I’m stoked to hear that you are concerned about your female partner. The first time can make both partners nervous, so I understand why you are worried about position and pain.

The problem with questions about pain is that it assumes that female pain during sex, especially the first time, is normal and expected. It is not. Assuming no medical conditions, sex should not be painful for anyone. Even if it’s a woman’s first time, it shouldn’t be painful. It should be pleasurable.

As an aside, as a female who has sex with men, I’ve been astonished when men shrugged off my discomfort and ask me to keep going, because they were about to come. Don’t be that fuckwad. It’s really fucking shitty to expect someone to endure pain or discomfort for your pleasure. You’ll be kicked out of her life, AND, she will tell her friends.

One of the challenges in having sex with women is that our society often demonizes female sexuality and desire. So there is a real possibility that she might not know what feels good to her, and if she does, she might not have the words to express it.

The first key is communication. Make it clear that at any time she can tell you to stop and you will. Ask if it feels good. Ask if she likes it. Ask if she wants you to do something different. Then listen and do what she tells you. If she seems to not have the words to explain, ask questions. And keep asking. Keep asking. It’s not uncommon for women to dodge answering questions about their sexuality–it’s been historically demonized and controlled. So she might be reticent at first. And if you never bring it up again…well, t’s like you never asked. She’ll likely think, “Yeah, he asked that, but then dropped it, so it’s really not all that important to him.” You have to ask and ask again. And again. And likely again.

The second key is foreplay. Why is it so important for women? And what does that look like?

Consider your dick for a second. Have you ever tried to fuck someone with a softish dick? If you have, you know how badly that works. If you haven’t, I’m sure you can imagine how badly that works.

The equivalent for women is being penetrated before being ready. Just like shoving a flaccid dick into a hole or hand is awkward or uncomfortable so it is for women who are penetrated before they’re ready.

The big difference though, is for women, early penetration is not only awkward, it can be downright painful—and that’s where the common idea that women experience pain their first time comes from.

So just as you have to be hard before you can have penetrative sex, she must be wet.

But her wetness and your hardness aren’t on the same trajectory. Your bodies are different. Your likes are different. So just because you are hard doesn’t mean that she’s ready.

So how do you help get her ready? For the nitty gritty details, click here for my free Make Her Moan Masterclass. Short version—stimulate her breasts and clitoris. Use your mouth, tongue, and fingers. Lots of kissing and eye contact. Expect to spend at least 30 minutes teasing, stimulating, and worshipping her body. Once she’s ready, you can penetrate her and it will feel good for both of you, not painful. Of course, you can also use synthetic lubes to help if needed.

If you follow the above about foreplay and communication, position becomes less important. Whatever feels good to both of you is what you should do. If I had to make a suggestion for the first time—or the first time with a new partner—I’m a big proponent of missionary, or anything face to face. It can feel really intense and connecting, which a lot of people enjoy. On a practical level, when you are face to face, it’s easier to gauge your partner’s pleasure or discomfort and adjust accordingly. You can talk, smile at each other, and check in easily.

Good luck!