So I'm 20 and my boyfriend is 28. I met him at a point in his life where he was going through his "hoe phase" and me being the person I am happened to fall in love with him. We eventually ended up becoming boyfriends early this year BUT he misses having sex all the time, with many different people. We don't have anal sex because when we have tried before it has been too painful for me, no matter how much lube or preparation I do. I've tried butt plugs and a dildo but they are still always too painful no matter how long I have them in or how long I use them for. My butt can definitely take more than it used to but there's always a certain deepness that no matter what is up there it hurts. Like a sharp, stabbing pain. Is this normal? Could there be something wrong with my intestines? I would really appreciate some advice because I don't want my relationship to to end because of this.
Well if your relationship ended because of this, it was never a relationship to begin with. Other members might give more practical advice.
This seems to be the fundamental issue. Your physical discomfort is the secondary issue. Seems like you and he need to have some deep discussions about your emotions for each other, how each of you define what a relationship means to you and see if you can agree to a an approach that works for both of you. Open communication is the foundation for any successful relationship. And your current situation requires honesty from the both of you to each of you.