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Pieter’s (24) question: Hey I have a HUGE problem…when I say huge, I mean huge… my boyfriend is very gifted, his Dick is so huge it just gives me chest pains. We’ve been dating for some time and we have only started having anal sex in the last two weeks. He is a top and is just way too big for me, in the sense that he can’t penetrate me…we’ve tried a few positions and nothing seems to help. I’ve been around the block and I know how to relax my muscles, but damn he is just too big. We’ve tried some Lube but nothing seems to help. To make matters worse he is not a bottom so changing roles won’t work. Please help because I just don’t know how to handle a pornstar!

Dr Dick’s response:

Having a ‘pornstar’ as a partner is the stuff of many a gay man’s fantasy! Perhaps try the following:

  • Purchase yourself a butt-plug. Preferably one that is large. The design of the butt-plug is such that your anus gradually widens the deeper you insert the butt-plug into your anus. In this way you should become accustomed to ‘large’ objects. Try 6 reps a day for at least two weeks. You can practice inserting it yourself or you can introduce it as a form of fore-play with your fiancĂ©.
  • Try to reframe the sexual encounter. Gay men often put a lot of pressure on themselves and their sexual partners to perform anal sex. This is because anal sex has become synonymous with gay sex. Most gay men see anal sex as the only valid form of ‘real sex’ between men and therefore place a great deal of pressure on themselves and their sexual partners, directly and indirectly. So perhaps a suggestion could be to remove your focus off anal sex for a short period and agree instead to focus on other, equally exciting ways to experience desire and pleasure with one another. I am reminded here of a case I heard about where a guy had a particular fetish for being f*cked in the arm pit. It may sound bizarre for many but at least he was able to find alternative ways to experience pleasure. Thigh sex, which is very popular amongst straight adolescents, is another option. Be creative and have fun while you’re at it.
  • It will only work if you really want it to. This may be a bit of an unsettling idea, but we need to explore all the alternatives. There is the idea that he can’t enter you because you are feeling conflicted about something: perhaps anxiety, perhaps fear, or perhaps anger. Try and think (and hold back the laughter for just a moment) what his ‘huge’ penis may represent or mean for you? How does it make you feel? Now, how would you feel having it inside you? What could that mean? What are you achieving by not having him enter you? Does he use protection? These questions might sound strange but might be helpful to consider. Those in the know maintain that if you really want it (him inside you) then it will.