Top and bottom problem, really need advice

[marshlander]

I'm going to do my best to ignore all the side issues on this one and try to address your questions. You should not have to suffer pain when you are having sex. It is supposed to be enjoyable! If he is hurting you, he is not being gentle enough, not giving you enough time to adjust to having him inside you. If he is being inconsiderate you can still experience pain even when you have used a ton of lube. For your own pleasure I assume you have tried practising solo? Take your time and use a dildo to explore and be very slow and gentle. If necessary, start small and work your way up to something that approximates his size. Work out what you like. Remember it is often all about getting the angle right and everyone is slightly different. If you can take a toy with no problem you should be able to accommodate your friend too. Again, experiment with positions until you find what works for you and don't let him use you like he's operating a battering ram!

As far as he's concerned, you can't live his life for him. If he is considerate of your feelings he will be getting on with his own homework too, but you can't enforce this. No doubt he is seeing that you, the supposedly more gay of the two of you, aren't enjoying being fucked. What encouragement is there for him to put in some practice when it is obviously so unfulfilling? I guess I can only wish you good luck!