Ask DeAnn: Help! I’m Too Big for My Girlfriend!


Hi, thank you for helping or trying! lol Where do I start? I can’t really talk to guy mates and don’t have a girl friends to talk to about it. I have been seeing a girl for the last 6 months great girl but a little closed off sexually. My issue is and always been I have a very large penis and I know guys say that and all but it’s really been a curse more then a blessing. Regardless of how much foreplay we have the sex has been really awkward with often she’s in pain or really uncomfortable I tried talking to her about it but she not comfortable. I do use lots of lube but it doesn’t last have you got any tips or advice? I love sex but I don’t want there to be this disconnect I must sound like a tool but any advice is appreciated. It was great when I was stripper but not practical in the love life! 

– Big Guy

Hey Big Guy!

What concerns me most about your letter is her unwillingness to talk about it. That indicates to me that there’s some level of discomfort or shame with sex, or a communication & intimacy breakdown between the two of you. You’ve got to get to a place where you can talk about this. Without that, none of my suggestions will work.

Approach her outside the bedroom, and invite honest conversation. Acknowledge that it’s uncomfortable. You need to empathize with her. She likely feels inadequate or broken. Society has told her that she should love a big penis, and not to reject your manhood lest she reject you as a human being. (I’m glad you’re smarter than that harmful message.)

Once you can engage in conversation, you’re going to need some practical suggestions you can throw out and give her the option to try with you, and some information that will help assure her she isn’t broken.

Physiology and the Pelvic Floor

Physiologically, the vagina can stretch. It’s designed to. That doesn’t mean it’s always painless (ask anyone who’s given birth). Some people just don’t like the sensation of stretching tissue. Sometimes anxiety about sex can cause the muscle tissue to tense up, making things even more painful. This is why it’s crucial to go slow. She needs to be very aroused. This will make the tissue more stretchy. You’ll need to engage in LOTS of foreplay.

You’re doing the right thing by using lots of lube. A hybrid lube will last longer than a regular water-based lube, so you may want to consider switching to one.

You need to gradually stretch the vagina and she needs to willfully relax the pelvic floor muscles. Don’t worry, the vagina doesn’t permanently get “loose” – that’s a myth. For this, I recommend Kegel workouts every other day, working up to daily, for her (and she’s got to actually do them). For best results, Kegel exercisers will help her learn how to willfully relax those muscles. Then it’s a matter of working up to your size.

Just like anal sex, it’s important to go slow and use stretching techniques to work up to the size of your penis. Use fingers and/or toys of increasing size, slowly, pleasurably, to relax the muscles when you’re together. I can’t stress enough the importance of going slow. If it seems like her muscles are tensing up, or she experiences pain with one or two fingers, stop. That’s a sign it may be a medical issue and she needs to make an appointment with a doctor.

When she masturbates, it’s a good idea for her to work up to regularly using a large toy internally, regardless whether she uses a clitoral vibrator externally. Start with toys greater than 1.5″ and then move up to one 2″ in diameter. Remember to go with non-toxic, non-porous materials. A chemical burn or severe infection from a cheap toy can lead to scar tissue, which doesn’t stretch. Here are some luxury toys from my shop to consider:

Positioning Tips for a Big Penis

First and foremost, you can forego intercourse pleasure for a while. This will take the pressure off of both of you. Instead, engage in oral/manual sex and bring toys into the mix. To heighten intimacy without intercourse, look directly into one another’s eyes and match each other’s breathing. Hold this gaze whenever possible. Physically stay close. Focus on sensation, pleasure, and each other. You may find this actually more intimate emotionally than intercourse. Then, slowly introduce intercourse back in.

When you enter her, take your time and be gentle. She needs to give you constant feedback about whether the stretching feeling is uncomfortable or pleasurable. One of you needs to stimulate her clitoris at the same time.

I talked to some fellow sex educators to brainstorm positions that might work. Here are a few to try (hat tips to Sarah, JoEllen, and Robin):

  • Rather than penetrating her, compress the penis between her labia, rubbing against her clitoris with lots of lube
  • Spooning, on your sides, with you supporting her leg or rubbing against her vulva/clitoris instead of penetrating her
  • Any position where she is on top and can control the depth of penetration and speed of thrusting
  • From behind with a pillow beneath her hips

With patience, good communication, and lots of practice, I’m sure you’ll both find a way to make sex pleasurable for both of you.


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