If she's aroused and wet enough, you've tried using lube for added wetness and there's still a problem with penetration, she should talk to her gyno about it.

See a counselor and deal with the emotional problems, particularly the fact that she violated your trust by screwing several guys behind your back, and you're understandably hurt and angry about that.

Whoops, my bad, she slept with multiple guys AFTER you broke up. Still, it's understandable why you wouldn't want to "go back in there" after knowing that.

Is she claiming that the penetration hurts her? I am a little confused...not sure I totally understand the problem. You know for a fact that she was being extremely sexual with other men after your break up? Have you asked her if she was having this problem with any of the other partners (I can understand if you don't want to discuss this with her but IMO it may be relevant info) if you are too painful for her to handle than she definately needs to see an gynecologist about this. That would be the first step.

I agree with Leather. being on the 'thick' side your should use lube. And getting her aroused will help with her lubrication and relaxes the muscles. I figure the pain was turning her off.

So, ahem, "sloppy seconds", the thought of multiple other dude's sausages being in there, has nothing to do with this?

What should you do...I don't know, man, maybe see a sex therapist or couples counselor.

From Teddy's post, I took it that it's not him having an issue with having sex with her, it's that she's having pain or discomfort with penetration.

Hello, sorry for taking so long to respond. Regarding arousal, I do everything I can to get her turned on. I love going down town. I perform foreplay, I try to initiate the sexual intimacy every time. The other night she was extremely wet but I still could not penetrate. She pushed me off and then got upset at the failure. I basically had to coax her back into being intimate and just masturbate her. I.generally have to make myself cum when masturbating b/c I do not cum easily for another person's hand. It takes her a while, not b/c I'm not turned on but b/c I just don't cum easily from another hand. When I am inside the vagina, I takes me a while to cum as well, which has caused problems in the past. I thought it was a good thing that I lasted long but I believe she took it as I wasn't attracted or turned on. Now regarding her past encounters, I do know for a fact that she was with several men. For a while, the only thing that upset me was the fact that she so easily gaveit up to them but it almost takes an act of congress for me to get anywhere. I have sense gotten the point of not focusing on things she did during the break up, it truly doesnt concern me. But it still hurts just a lil that when I try to be intimate, I get turned down most times and then when we do try, sex just doesn't happen. I know some of you maybe thinking that she is cheating, but I have insurances in.place that tell me she is not. One.of them being she's either staying at my place o4 her parents, where she moved back to. Her parents house is not one where sneaking out is not an option, trust me. She wasn't having this promblem with the other guys though. Like I said there was one guy in particular that she was having sex with several times a week,.multiple times a day. I have mentioned this in.a argument and she fired back that he was smaller. I have since then promised to leave the past in the past. She truly acts as though she wants us and our life to continue. Everything else in our relationship is going well, except of this one area. I don't want to make it seem.like all I want is sex but sex is a big part of a serious relationship if you crossed that line already. m not a cheater, so I won't go looking for another person to fill the void, but its making me feel like I'm inadequate. I love her beyond belief and I just want to make her happy and please her to the best of my ability. Igive her massages daily or when she asks for them. You would believe that alone would be great start to intimacy but its not. I'm at a lose here.

I hate to say this , but i see more problems here then just sexual. Maybe she regrets all those other guys and feels dirty and that is causing issues. Maybe try some counciling if you cant talk together about the real issues that seem to be bothering you both.

Just a thought and wish i had better advice.

Just sayin you are young and if you cant get those old memories out of your mind you should maybe move on.. You would be surprised how much better it is being with a woman that you dont have those messed up memories to deal with.

Go for the clean slate why try making a bad situation work when you dont have to.

My original advice was to have her go to the gynocologist and now I am thinking that maybe you could benefit from going with her. I myself would wanna hear first hand what the doc had to say.
If the gyno fails to find a solution to the problem...or if he offers things the two of you can try and they do not work...then I submit to you there must be some deeper issues than what she is copping to. She may not even be aware herself of exactly what is going on with her. The problems could be totally subconscious. I think you two would have nothing to lose by seeing a therapist or a counselor. Get everything out on the table. I hope you are able to figure things out and good luck to you!

I'll second the therapy option.

I don't know why she had no problem giving it up to other guys, while it requires an act of Congress to make her want to give it up to you. Maybe they were more aggressive, simply TOOK her, while you're more touchy-feely, gentle and like to take your time, which doesn't turn her on; maybe she likes it more rough. I don't know.