Sex advice/I can't cum.

[tyty]

So guys, I am a long time listener. First time thread maker.
I am in a weird situation: I am finding it really hard to cum when I have sex. Little background: 27/m/ I do give a huge shit about this and I have only had 3 relationships spaced out over years. So, I've spent a large part of it pleasuring myself. Now that I have someone as sexual and a little kinky as I am, I get so excited pleasuring her but it never pays off in climax for me. I have tried not masturbating at all in between sessions and that has not worked out so far. So, I look the KATG'ers for advice.

Thanks, all.

[amyuilani]

Tantric sex. And stop jerking off.

[DWarrior]

maybe?

[stabbyhappy]

Ask yourself these questions:

Are you genuinely sexually attracted to her?

Does she know how to please you?

Is something in your head holding you back?

Is she on the same page as you regarding the status of your relationship?

Are you focusing everything on her pleasure and not on your own?

In the mean time fuck her until the cows come home. The opportunity might not come around again.

[word]

One of these is the answer

Originally Posted by stabbyhappy

Ask yourself these questions:

Are you genuinely sexually attracted to her?

Does she know how to please you?

Is something in your head holding you back?

Is she on the same page as you regarding the status of your relationship?

Are you focusing everything on her pleasure and not on your own?

In the mean time fuck her until the cows come home. The opportunity might not come around again.

[Ubertapper]

Could be the way you are masturbating. If you are jerking so hard that it no longer comes close to feeling like a pussy would, you may be disillusioning your dick when the real thing comes along.

[tyty]

See below, thanks everyone.

Originally Posted by stabbyhappy

Ask yourself these questions:

Are you genuinely sexually attracted to her?Yes, I don't see this being it. I think about her when I masterbate

Does she know how to please you?This may be a portion of it.

Is something in your head holding you back?Obviously, this is the one I'm worried about. Having a problem like that takes time to deal with.

Is she on the same page as you regarding the status of your relationship?We have been very honest and upfront about everything I don't think this is it.

Are you focusing everything on her pleasure and not on your own?This is another possible reason. I spend a lot of time getting her off and it might be affecting me.

In the mean time fuck her until the cows come home. The opportunity might not come around again.

[Lanfear]

Originally Posted by Ubertapper

Could be the way you are masturbating. If you are jerking so hard that it no longer comes close to feeling like a pussy would, you may be disillusioning your dick when the real thing comes along.

This! From what I hear from Rev Jen and read on Dan Savage: Training your cock to only react to a deathgrip is a very possible reason for your problem.
Savage Love by Dan Savage - Seattle Columns - Savage Love - Dan Savage - The Stranger, Seattle's Only Newspaper

And as a girl let me speak for your girlfriend: "Ouch this hurts and this is going on way to long to be fun" and "Oh boy he really must find me unattractive/fat/dumb/untalented/... if he doesn't come from sex EVER"

[marina]

Do you ask her to do things during sex? Maybe she's not helping you out as much because she doesn't know what you want.

Another thing might be nerves. Being comfortable enough to cum in front of another person isn't just a girl issue. I've had guy friends who have the same problem. They won't cum until they feel safe with the other person.

[crecentroll]

Put it in her butt. Then if you cum, you know you're just gay and there is nothing wrong with you. Except being gay, of course.