How can I have sex with my boyfriend without it hurting?

We don’t know you or your boyfriend.

We also don’t know what you consider “sex.”

What people that study human sexuality know is that fear, discomfort, shame, coercion, and dishonesty greatly decrease the possibility of pleasurable sex for all involved parties, however you define sex. People from conservative, repressive, bigoted, and sex-shaming backgrounds usually encounter difficulties giving, receiving, and reaching pleasurable sex.

The good news is that people can overcome these problems.

1. Know yourself

Yes, I am talking about self pleasuring. The best way to feel good during partnered sex is to know what feels good to you and to be able to communicate that information. If you don’t masturbate, you’re going to have a very difficult time doing this.

2. Confidence

I don’t mean arrogance or vanity. I simply mean knowing that you’re attractive to your partner(s), knowing your partner is / partners are attractive to you, and knowing you can make each other feel really good. No boasting or pretending is necessary.

3. Integrity

Most people find it very hard to deal with people they don’t trust or respect. This is exponentially more difficult when you’re (1) also naked and (2) looking for romantic/sexual connection. Whatever issues or problems are affecting your relationship outside of the bedroom will definitely affect your sex life. It’s exceptionally difficult to be intimate with untrustworthy individuals. If you’re the untrustworthy individual, fix your problems before you get naked with anyone.

4. Honesty

Can you tell someone what you like without getting defensive, angry, or embarrassed? Can you tell someone what you don’t like without attacking the other person or accusing them of being bad at sex? I’m not saying you have to be perfect, but you do need to be able to communicate your desires in a relatively straightforward, unambiguous, and considerate fashion.

5. Medical Issues

If you have any physical/mental problems that can compromise your enjoyment of sex, you need to get these addressed by reputable and credentialed medical professionals.

6. Relaxation

If you’re tensed up, worried, or uncomfortable, any sort of partnered sex will be problematic and unpleasant, especially penetrative sex. A little bit of nervousness is to be expected, especially if you’re trying something out you haven’t done before. If you’re the one being penetrated, you set the pace. Your partner needs / partners need to understand and respect this. You also need to have access to space that’s comfortable and private where you won’t be interrupted.

7. Protection

This means barrier methods for genital contact, effective birth control if you and/or your partner(s) can get pregnant from the sex you’ll be having, additional lubricants that don’t compromise barrier protection, and safe words / procedures for ending kinky encounters quickly and without question.

8. Creativity

Obviously you know that penetrative sex is not the only kind of sex you can have. If penetration is not to your liking now, temporarily, or permanently, there are other ways to give and receive pleasure. Use the biggest sex organ you have (your brain) to find exciting new ways to please yourself and others.

9. Consent

Simply put, anything you don’t want to do, you don’t have to do. The same goes for your partner(s). Make sure everyone’s given their go ahead before trying something. This doesn’t have to be awkward, robotic, or unappealing. Give and withdraw consent in a sexy, flirtatious, and playful fashion and no one needs to get their feelings (or themselves) hurt. Again, if you’re going to try something you haven’t done before but would really like to, take it slow, let the penetrated partner set the pace, and give feedback (not just words) that lets your partner(s) know unambiguously what works and what doesn’t.

10. Patience

If something’s not working out right now, take it off the menu and see if things won’t be better, easier, or more comfortable at another time, in another location, or with another mindset. There’s no need to rush into something that won’t be good for all involved.

I wish you and your boyfriend all the best, most passionate, most joyous sex possible.