top of page

Do You Have a Big Dick Boyfriend: Top Tips for Pain-Free Penetration

by Isabelle Hartley, BedBible

If you’ve ever gone to get down to it and been taken aback by the sheer size of your partner’s penis, you might have experienced a mix of fear and excitement, but sometimes that can turn into some serious discomfort and even pain.

While being too well-endowed might sound like some kind of humble brag, it’s no joke if it puts a stop to the fun! Although there has often been a ‘bigger is better’ mentality in society, that really isn’t the case, and it’s much more about compatibility between the sets of genitals involved.

Image Credit: Photo by Cottonbro studio / Pexels

Unfortunately, genitals don’t always match up size-wise and can need some modifications to make sex comfortable and enjoyable. Fortunately, we’ve got some ideas that can help, so there’s no need to despair or give up on penetrative sex altogether.

In general, penetrative sex should be possible with most penis and vagina sizes — the vagina is designed to stretch, but that doesn’t always mean it’s easy, and it can require some practice to create the right circumstances and find what works for you.

Most importantly — sex shouldn’t be painful! Dyspareunia — pain during sex can have many different causes. If you experience pain during sex, you should always get checked by your doctor or gynecologist to make sure no underlying issues are causing the pain.


So there’s no set definition of what’s too big when it comes to penises — it’s more about how your vagina and your penis work together. If you have no underlying health issues causing pain when you have sex and notice it only when you have sex with a bigger-than-average penis, then size could be the issue!

  • It could be that their penis is too long and bangs against your cervix when they thrust, which can be very painful, although some people do enjoy cervical stimulation when done in the right way.

  • You might find that he is too girthy for your vaginal canal, meaning it’s painful or impossible for him to enter you.

There could also be psychological or physical factors that are interfering with your arousal and preventing your body from becoming ready to receive your partner’s penis. If you have been checked for underlying issues and there are no other issues apart from size, this post will walk you through some things you can try to make sex more enjoyable for you both.


First of all, you have to be able to communicate to your partner that you are in pain and you need things to slow down or stop altogether. You also need to communicate with each other during sex when things start to get painful so you can direct him on how hard to thrust or which angle feels best. But it’s not all about you! Your partner can help by asking questions and paying attention to your bodily feedback.


Stress and fear cause the muscles in your vagina to tense up, making your vagina tighter and making penetration more difficult. If you have experienced pain from intercourse in the past it’s natural to feel fear — fear is there to protect us from pain and damage after all!

To help relax your mind and your muscles try to incorporate relaxation techniques into your foreplay. This could include some deep breathing in which you feel your breath traveling to your pelvic floor and expanding and relaxing the whole area, a full body massage with some massage oil, or creating a relaxing atmosphere with soft lighting and calming smells.


Foreplay is crucial in helping the vagina to dilate and release the natural lubrication needed to help things along. Your vaginal canal can also lengthen in preparation for penetration. These factors are especially important when faced with a whopper, so you should always make sure you are fully aroused before attempting penetration. Some great options for foreplay include kissing, nipple and clitoral stimulation, fingering, oral sex, or whatever feels good for you! Bullet vibrators or a wand sexual toy is a great option for partnered foreplay, as it is easy for your partner to use on your clitoris or nipples for some added oomph!


When you are fully aroused from all the foreplay, you can try getting yourself ready for penetration using increasing sizes of dilators or a realistic dildo. This will ease your brain and body ready into penetration with your partner’s penis rather than jumping in at the deep end. You can take it slowly here and give yourself time to adapt to the feeling and time for your body to relax and feel safe. You can also choose a Yoni egg or kegel vibrator.


You aren’t alone in this experience! It’s so common that now some clever cookies have created Oh Nut— silicone donut-like rings that are worn on the penis to prevent your partner from thrusting too deep. The pack comes with four stackable silicone rings that sit snugly at the base of your partner’s penis, and you can alter the depth they can thrust by adding or taking away rings. A pretty nifty solution to a pesky and painful problem! They got a near-perfect score from our tester!


Lubrication can make any penetration feel so much better but is particularly important when dealing with a large penis as the size can cause push against the vaginal wall, resulting in friction, or even lead to small vaginal tears, and no one wants that! Be sure to apply plenty of water-based lube before starting and reapply as necessary.


Yes, we’ve come full circle back to communication because it is just so damn important, as is taking it slowly. Start by having your partner insert just the tip and give your body time to adjust to the feeling. Increase the depth slowly as you feel more comfortable, making sure to tell your partner when you are ready for more and when you need more time. The last thing you want to do is rush, as any shocks can cause you to tense up even more.


Positions, where the penis owner is in charge of thrusting, are probably going to cause the most pain for you. It is quite difficult for your partner to know how deep they can go, and it’s easy for them to accidentally thrust too far, leaving you in pain and feeling guilty. However, that doesn’t mean you can’t enjoy an exciting range of positions — you just have to be a little more tactical about the ones you pick.

  • Vulva owner on top positions allow you to control the depth, speed, and angle of penetration, so you can find what works best for you.

  • The CAT (coital alignment technique) is another great option. The man lies on top of their partner’s hips, with their penis pointing down into their partner’s vagina. Instead of thrusting, they rock back and forth, with the tip of their penis stimulating their partner’s vagina and the base of the shaft grinding against their partner’s clitoris.


  • Never ignore the pain and try to push through. Pain and fear are our body’s ways of telling us we are not physically or psychologically okay and ignoring these cues can be damaging.

  • Do not use anything to numb or desensitize your vagina for the same reasons as above — it’s really important to be able to listen to what your body is telling you.

  • Don’t be afraid, embarrassed, or shy to talk to your doctor or a gynecologist — they should always be your first port of call when you experience any pain during or after sex.


bottom of page