I’m really excited that I had the honor to coach someone before his first time having PiV with his girlfriend! Because he is a teenager and couldn’t afford my rates, I took him on as a client pro-bono. This was a really rewarding experience for me, and I asked him if he’d let me share this story so that we could share what we learned with anyone else in the same situation.

This client (I’ll call him “Charles”) had been following my work for a while, doing his research on how to pleasure his girlfriend. When he reached out to me, I think he expected that I’d give him some sex hack to “blow her mind”. What we ended up talking about is having good sexual behavior and communication to have the sex life they both deserve.

Many people have a lot of anxiety before their first experience with penetrative sex, and Charles was feeling a lot of that. They put a lot of pressure on themselves for it to be good, and they have hyped-up expectations of what it will be like. In reality, most people have experiences closer to, “Okay, this feels interesting…how do I make it feel great?”

I gave him advice that I give a lot of my clients: You are responsible for your own arousal and pleasure. The idea of “you have to make her come” is only going to cause more anxiety for both of you. The goal is to focus on exploring and enjoying each other, and discovering what’s pleasurable.

The difficult thing with first-time penetration in this day and age is that you have constant access to porn and masturbation. So what you’re used to is whatever porn you’re into and the “virgin death grip” of your own hand. There’s nothing wrong with that, but you’re not going to reproduce those same conditions in partnered sex.

I talked to Charles about why it’s important to talk openly with your partner before sex. Share what arouses you, how you like to be touched. Tell each other how you masturbate. Once you both talk about what works for you individually, you’ve started to build a toolbox of things you can try while you play.

Here are some of the technique tips I shared with Charles:

  • Let’s end premature penetration! Spend time getting your partner fully aroused with touches and massages.
  • Use lube!
  • Learn how to masturbate with condoms on, to get used to the sensation.
  • As you’re transitioning from foreplay to penetrative sex, rub the head of his penis onto her external clit to get her aroused and excited about penetration.
  • It might be painful! Make it clear that you’ll stop at any time.
  • The great thing about sex is that you have the chance to do it over and over again. Instead of focusing on having a perfect first time, establish good practices so that you’ll have a great lifetime!

You’ll be happy to know that Charles  reported that his first time “went pretty all right”! Thanks in part to the conversations I had with him, his expectations were aligned with what happened. Remember: Sexual confidence is built over time, but if you have the right model of being kind, giving, responsible, and communicative, then you set yourself up for a lifetime of great sex.

We’ll follow up with Charles and his girlfriend next month, so stay tuned for Part 2!