Q&A: Help! I Can't Have Penetrative Sex

Updated : September 10, 2025

'Dear Sh!

I've been trying to lose my virginity, but I can't. We have tried so many times, but I always stop him before he goes in all the way because I can't handle the pain. He says that I am very tight. I get very wet, but then this happens, and I get tense, so then it takes time to get back in the mood again. I have used a dildo before and it was ok, but wasn't as big as his dick. What can I do? Does it always hurt this bad?'

Hi there,

First, take a deep breath and repeat after us: Sex should not hurt.

It’s common for people to say that losing your virginity is painful. It's true that first-time penetration can be painful. It is also true that not everyone experiences pain - in fact, some folks have pleasurable first times.

First-time p-i-v pain can be because of nerves, a strong hymen or a lack of warm-up or lubrication.

Cycle of Pain

Once you’ve tried it once and it’s gone badly, the second time can be even worse. You are likely to be nervous, tense and worried about more pain. This is known as the cycle of pain.

Trying to persevere and grit your teeth through it will be detrimental to your future sex life, so don't do that. Instead, let's look at what can help make it a better experience.

First of all, we recommend booking a vaginal check-up. This is just to check that all is well.

If all is well with your vagina, you may want to speak to a psychosexual therapist next. The cycle of pain can sometimes lead to a condition of Vaginismus, or a tense pelvic floor.

For now, we recommend taking p-i-v penetration off the menu. Your brain has come to associate sex with pain and wants to protect your body by tensing the pelvic floor. You have no conscious control over this - your brain is in control. The job is to teach your brain that sex can be pleasurable.

Kissing, touching, stroking and bringing each other to orgasm are ways to enjoy sex without penetration.

It’s essential to use lube for all sex play, including finger and toy play. Even if you feel wet, additional moisture can go a long way.

Practice Penetration During Masturbation

Try using a slim vibrator or dildo to stimulate yourself during masturbation. This will help build your confidence, and your brain will recognise sex play as something pleasurable.

Take some time to practice by yourself. Make sure you are super-turned-on before attempting to insert the tip of your chosen toy. The goal isn't to glide the entire shaft in. No, this is an exercise in learning how to relax your pelvic floor so you can experience penetration without pain.

Working slowly and over several solo sessions, you'll be able to insert a little more over time. Once you are comfortable inserting your slim toy, it's time to use a toy with more girth. Start the process all over again (tip only) and work your way up to being able to insert the shaft without pain.

The Ohnut For Comfortable Penetration

When you decide to try p-i-v penetration further down the line, we recommend a position like woman-on-top, where you can be in charge of speed and depth.

You might also find the Ohnut useful. A soft, body-safe and flexible wearable, the Ohnut slips onto the penis shaft and acts as a buffer for penetrative sex. It's essentially a "stopper" and stops the penis from going deeper than you are comfortable with.