I'll leave this one to the more experienced members, but I am interested in the answers as well.

[QUOTE=sunshowers;238887]My boyfriend and I recently had sex for the first time - for me if was my first time ever, he's not very experienced but he had done it before. We're young, but not teenagers. We have probably made 10 attempts and only been mildly successful once. Every time we're ready to do it, he puts the condom on and loses his erection.

He is uncircumcised, which seems like it could have something to do with it. The tip of his penis is SO sensitive and used to feeling pleasure in such an acute way that it seems like the condom dulls his feeling just enough to take away the excitement.

I'm getting frustrated...I hate to have to think about his penis like this volatile entity that needs to be obeyed and can easily change its mind any second.

It seems like there could be other issues at play, too - he says he needs to be EXTREMELY turned-on to have sex, which is just not something I've experienced in a man before. He says that most of the time he just doesn't really want to do it/think he can do it. A little foreplay, making out, touching, oral stimulation, and usually the man is ready to go. I've given him blowjobs that last as long as possible before and he has never cummed. He's never cummed once so far (we haven't been hooking up for that long, but we've had quite a few sessions).

My theory - a combination of being uncircumcised (i.e. extremely sensitive) and having sort of a mental block about the act. He'd done in a few times with some random girl who was a friend that he didn't even like, so this is the first time that there has been love or emotion involved in the act making it about more than just sex.

Does this seem like a physical or a mental problem?[/QUOTE]

I really think you're over analysing this. Basically he's not used to wearing a condom.

I've experienced this a few times and its something that he will eventually get used to.

Firstly be prepared for the question,,, which he might well ask if only out of frustration,, and that is "will you do it without one". Be emphatic and don't give any room for manouver. He needs to learn how to shag with a condom end of story.

Next time after he puts the condom on instead of rushing straight on to actual penetration, just concentrate of keeping him hard. Rather than concentrating on his cock, just snog for a little while and let him touch you. Don't try and put too much concentration on his cock.

If he's usually erect during foreplay then just keep doing that only with the condom on.

Also I don't know if its something you want to do together but it'll help if he tries masturbating while wearing a condom.

You put the condom on him. That makes it part of the play; you continue stimulating him; you know it is on right.

Take sarah's advice: do not fall for the old line of needing to do without. You need it with.

There seems to be a trend recently that guys in particular, and no doubt couples, operate under the misguided misconception that the way to a climax is from lots and Lots and LOTS and LOTS of stroking. WRONG! The path to a climax is from making out lots and lots. When he has been brought to the brink of an orgasm yet can still maintain control sufficient to move around and get into position--place the condom on him as Brandye suggests--not before.

> He is uncircumcised, which seems like it could have something to do with it. The tip of his penis is SO sensitive and used to feeling pleasure in such an acute way that it seems like the condom dulls his feeling just enough to take away the excitement.

Think about this a minute: a condom lowers every guy's sensitivity. A "natural" guy's penis has a layer of insulation that is missing on circumcised men. A good method of increasing his sensitivity is to retract his foreskin before rolling the condom on.

A second method is to dab a bit of lube on the glans ONLY so that it has a bit more wiggle room inside the condom.

Give one or both of these methods a try and report back, please.

If you apply the lube and/or roll the condom on, you can continue to keep his arousal peaked and have some fun in the process.

Oh! and lastly, what if he does lose his erection? No harm no foul. Just rebuild it. Doing so should continue your enjoyment particularly if you can get him squirming and moaning. :) Please understand male physiology, erections come and erections go. When one is lost this does not mean that your love making is at an end. Not at all. Just fall back, work some on Necking and Petting and give him a few moments pause then work on reestablishing the erection.

BTW, if you want a long session, build and let subside more than once. You'll drive him wild and your enjoyment and his continue.

Bah! No condom = no penetrative sex - period.
He still has his hands and his mouth and so do you.
Get busy!

Sex begins in the mind and hydraulics are notoriously finicky.

Do The Program and Body Worship and he'll be so hot that even his penis won't notice the condom once you've slid it onto him. Add a lubing up and then go for it. Capture his mind and don't take his penis's lack of cooperation as your answer.

by way of illustration: I and my partner attended a nice 'play party' last night. The lady said to him "you can do me bareback". To this he thought, but did not say, "Oh, Hell No!". He did not take her up on her offer. Condoms are REQUIRED in all sexual situations outside of monogamy/monoandry. It is how the world works now.