I’ve been seeing a really great girl for about 6 months now. The issue is, and always been, I have a much larger than average sized penis. I know it’s supposed to be a good thing and all, but it's really been a curse more than a blessing and particularly with the girl I’m seeing now. Regardless of how much foreplay we have the sex has been really awkward. Often she's in pain or really uncomfortable. I tried talking to her about it but she’s not comfortable discussing the details. 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.
Having a big dick is definitely a struggle that many find difficult to empathise with, but I don't think you sound like a tool for complaining about your tool.
The first thing you need to do is to stop thinking of foreplay as foreplay.
Oral sex, manual stimulation, playing with toys etc. are all just other kinds of sex and don't have to lead up to penis-in-vagina (PIV) penetrative sex. Without PIV sex you still can work toward pleasure and orgasm together but use other techniques to get there. Taking this painful kind of sex off the table for the moment might allow for both of you to relax a little and begin feeling more comfortable talking about and exploring sex.
Open and honest communication is the single most important factor in building and maintaining healthy and satisfying relationships (and having good sex). So you and the girl have to practice talking about these things together. One good place to start—instead of asking her about the pain she is experiencing during sex, why not ask her about what does feel good? If she refuses to have any conversation about the pain she’s feeling when having sex with you, then I simply don't think you should be having sex with her.
After trying this out for a while sex will no longer be this uncomfortable, painful, awkward thing between the two of you because you’ve been sharing relaxed and pain free orgasms. Then you can work toward making PIV sex pain free too.
Something to consider is if the pain and discomfort she’s feeling is more severe in comparison to any other girls you’ve penetrated, it might have nothing to do with your dick at all. She could be suffering in general with dyspareunia (pain during and/or after intercourse) or with a condition such as vaginismus or vulvodynia. If this is the case you should encourage her to see a doctor as such conditions are treatable (see a list of resources below).
But if the case is that the pain she feels is specific to your penis AND you can agree to start working on better communication, then one thing you can do together (or she can do on her own) is play with insertable toys of varying sizes. Slowly with time and patience you can work together to have her vagina get used to taking bigger and bigger items. This is partially a psychological exercise, as much of the pain she experiences in sex is probably related to feelings of anxiety about your size. When women are anxious/stressed/scared their vaginas can respond by tightening up or clenching, and this will greatly impact how much pain she feels. It's also a physical exercise as it will stretch and strengthen the muscles in the walls and opening of the vagina.
The key to making this possible is to find out what positions work for you two together, so some trial and error will be necessary. You want to avoid positions in which penetration gets very deep (eg. doggie), keep pumps shallow and try positions in which the girl has more control over the depth and speed of penetration. Chances are with time, patience, slow and gradual increases and a little bit of lube she'll end up loving your big dick. If it doesn't work out, remember there are plenty of size queens out there who will take it nooooooo problem.