I’ve been seeing a guy for the last 3 or so months, everything seems to be going great and I really like him. However, every time we get down to actually having sex he “can’t get it in” for want of a better phrase. We don’t have this problem when I top him and I just don’t understand why it doesn’t happen the other way round. I haven’t had this problem before when I’ve bottomed with other guys which is what really confuses me. He’s been really patient and we’ve tried taking it slowly, but still no banana! I feel really comfortable with him, and I can tell that he really wants to do it, which reinforces my will to do it even more. He isn’t pressuring me into anything, I’m just getting extremely frustrated at the fact that I really want to do it but cant. Have any of you got any tips as to what the hell I could do/is going on? All and any advise would be greatly welcomed.
What about using a dildo first to prep yourself open? That's about all I can think of, you're clearly not new to this as you've said you've had no problem with other guys, so not going to suggest the obvious things.
Like Zaio said, it sounds like you might need more anal play for yourself. Also, you do need to help him in at least somewhat. Does it hurt you, or can he just not get in, period?
Is it that he can't get it in, or that he's having difficulty being erect enough to achieve penetration? They're different issues, and if it's an issue of being erect enough, it's possible he might be somewhat inexperienced or otherwise not (consciously) comfortable enough, because the ability to get and sustain an erection is as much psychological as it is physical. If that isn't the issue, then all of the suggestions above should help.
Thanks guys, think we'll just have to do a little bit more anal play, just to start things off a bit more. We've tried all the other suggestions (more lube, changing positions ect) and it hasn't really helped, and he seems hard enough...... It'd just abit annoying that this hasn't happened with other guys I really wasn't that into, yet when I meet one I really like it does, infuriating!