Going soft

[princealbertofb]

I think it could be that you are really afraid of hurting him. The advice given here about preparing him well with either fingers or smaller objects sounds like good advice, just to make sure that you are aware that he's ready and won't hurt if you try penetrating him. I think it's the anguish of the possibility of it hurting him that is causing your loss of stiffness. You could also, as suggested, try just masturbating together, or even try a cockring?