My boyfriend of 5 months has a very promiscuous past, he has been with over 30 other women and he only just turned 19. When we first started going out I would go down on him, vigorously, trying to make him . When he realized that was my goal, he told me that while he enjoyed the act of me trying, he has difficulty that way. I took that as he thought I wasn't very good at it, which has never been a problem for me, and kept trying for months, if he "has difficulty" that means it can still be done, right? Recently I got really upset after trying for over an hour and he told me that he just can't finish that way because one time he was having sex with a girl and while going down on him, she bit him, really hard, and for no apparent reason. Is it possible that that experience could keep him from finishing when I go down on him? Is there anyway to overcome something like that? The ONLY way I can make him is during actual sex! But he must be able to get himself off when he goes at it alone!

Why don't you forget about fellatio and focus on other sexual experiences? :)

I think maybe he is getting it too often from someplace... maybe someone else.

Really, if its only once a day, he should not have any problems getting off that way... seriously, I'm a guy telling you this. The more often you get off a day the harder it is each time up until you can't any more. Everyone has their own technique... no two people do it the same from my experience. Yeah its possible to be horrible... but I haven't experienced that. Not when she was entusiastic. Even from women who were just learning and didn't have a clue yet. The woman enjoying it is half of it right there... the other half is experience.

Can't say I understand his problem. I would kill for my wife to enjoy it or even do it. She hates it and won't do it at all. Maybe its just not your mans thing. People enjoy cuming in different ways. Maybe he feels more connected to you during intercourse. Connection is a very important part of sex. Don't take it personally.

I hate to be graphic but how do you want him to finish. If you want him to finish that way perhaps you could get him close with intercourse and then right before he has an orgasm you could go down on him.

He needs to understand its not always about him, if that is important to you he should be willing to try anything for you.

I know if someone bit ME during oral sex, I'd have a hard time relaxing enough to orgasm.

Give up on fellatio and focus on other parts of your relationship.

Some men find the pressure that can be obtained by oral sex is not enough to orgasm with. Not every man loves it.

He probably told you the biting story because he did not want to make you feel bad for not being able to finish him off.

If it is true,I would certainly be reluctant to have anyone 's teeth near my penis.

Don't over think it too much ,not everyone is the same.

There are numerous other ways to show you care.

I agree with Choux and Synnen.

Also, just an aside. I don't think people do things like that for "no reason." I'm not saying he deserved it, but she must have something on her mind. It seems odd that he doesn't even guess why she might have done that. I'd want to know! So I guess I'm wondering if he's in denial or not telling you everything. Just something to put on the back burner.

Oh if you don't know what you are doing its going to take a lot longer... I always explained to the wife its like chasing a slow moving train... if you stop its going to get away from you, and if you spend too much time admiring the flowers its going to get away from you...

But I'd rather have an enthusiastic woman who doesn't know what to do yet than a woman who does but does it half heartedly anytime.

Like asking mentioned... I wonder if he grabbed her hair, ears or the back of her head when he was close and almost choked her? I'm willing to bet that's exactly what he did... very, very, very few women want or like that.

LOl! I'm sorry that was interesting all the responses... um I don't want to hurt your feelings at all not intended.. but it may be that he doesn't necessarily enjoy the way your doing it... you may be great to someone else.. but he may like it done differently... if a guy is enjoy the head.. IT"S going to let you know.. he's not traumatized please... when your doing it.. just be sexy ask him what he likes... try different things... yummy

Different people like different things sexually. Do what gets him off and stop trying to do the things that he tells you doesn't. He will love you more for that.

I think it could definitely affect how much he enjoys oral.

No need to make it about you, stop beating yourself up.

I'm sure the pressure of you 'vigorously' trying to get him off isn't helping either!

That's tough. I wonder, though, if the biting story is true. It might be, but I'm inclined to agree with Asking. I think there may be some things he's not telling you about his past. If he was abused through those means, the trauma could reproduce itself in the way you described. That would also explain the promiscuity. It is not uncommon for children who were abused to act out sexually.

This is will communication comes to play. Just like us females guys like things done a certain way.

If you don't have a clue what your doing he should be able to guide you to his liking. Also, if had a bad blow job in the past that resulting in biting and it was so traumatic for him, I don't think he would be allowing anyone down there for that matter especially if he knows your inexperience.

Don't let his number of sexual partners get in the way because people could sleep with 30 people and still have no clue about sex. I learned and got all my sexual experience from one guy so a number is just a number and really means nothing towards experience.

I remember dating a guy that didn't have a clue on how to please me orally and he use to talk about how many girls he slept with but when it came down to oral sex he didn't know squat. I taught him things and he wasn't a easy student but in the end he caught on and even though we didn't last I am sure the next girl after me was pleased.

So talk about sex with him go over what the two of like and dislikes. It not all about him you deserve to be getting please too.

Pay more attention to what gets him off, and don't worry about what doesn't. Why is it so important that you get him off orally any way?

This sounds as if its more about you, and what you want, than pleasing him, and that's what you need to tell him.

Don't be so vigorous. Be gentle. Basically if he can't finish that way, so be it. Maybe in due time he will if you're much more gentle with him. If done properly men love it. If done way too vigorously, most don't like it that way. Let him finish the way he wants to. At 19 and having had 30 women so far, he's extremely promiscuous if you ask me.

Put a finger in the brown eye while doing it mabey it will help

Ask him how the other 30 did it. You can always use toys for him:)