How do I talk to my guy about his "shortcomings" while staying sensitive to his obvious embarrasment? (NSFW)

How old is he? Is he in good physical shape? Is he taking medication, or drugs in general?

We’re still pretty young, he’s only 19. He’s an average male, used to play football so he’s still in pretty good shape and the only drugs he’d be on are those muscle powders.

I also might add that it’s not like he’s shy. He’s a typical guy, all over me when he wants to be but has never really tried to make any moves beyond making out…. I’m not sure if that’s a sign or what but everything’s starting to add up right about now..

I’m not sure it’s something you should talk to him about. If you’re going to break off that type of relations with him for that reason it’s going to be hard on him…. um… no pun intended.. for realz.

It’s not that I want to break it off just because of that but beyond the sex I see it as a trust issue. I think we’re both mature enough and should trust each other enough to talk about it without him just being embarrassed and me telling all my friends.. I would love to figure out how to fix this because I feel like I’m in a nightmare and this can’t be happening.

This situation is not at all unusual, so don’t feel alone about it. It could be a whole list of different things causing it. In order to have a better outcome, you’ll have to get at the root of the problem. That means talking about it.

It seems to me that if two people are willing to make the attempt in the first place, they ought to be able to discuss it. Just be direct and nice about it. Say something like “Ok, so obviously the sex thing hasn’t been working so well between us… is there anything we can do about it? Anything I can do differently? Maybe we just need more practice.”

Really? I thought @AstroChuck was older than that.

@filmfann Ooooooo ‘high five’
I would agree with Augustlan, just discuss the matter in a light hearted way making certain to assure him that it’s fine. The last thing you want to do is place additional pressure on him.

I second Augustian’s advice. You need to not think of it as a problem on his part, or even a problem at all, but something that needs more work. Maybe he’s nervous—I mean, if you guys have been friends forever and are trying to have sex, that can be a nerve-wracking first step into something more serious. Are you just ignoring him after that happens? Because that’s not the right way to go about it, try other things if that happens. Oral, etc, there are lots of other kinds of sex and if you help him in other ways, you might be able to find out if it’s sheer nervousness about intercourse or a physiological problem.

1) Are you guys Catholics?

2) Did yopu do all you could to stimulate him further?

@Zendo What effect would being catholic have on the situation? I ask out of curiosity, not offence

@Nially_Bob If you don’t know you must not be catholic dude. Catholics are so guilt ridden over sex that many times guys lose erections over the guilt of having unmarried sex.

and I never tak offence over internet interactions anyway…

Are you pushing the sex or is he?

Maybe he doesn’t see you that way. Didn’t he have to get drunk the 1st time? Maybe he is just embarking on this adventure because he thinks you want to. Women are lucky when it comes to pity sex. We can be mentally and emotionally disconnected with a well placed “Ooh, baby”. Guys have to actually perform.

If he is really your friend, give him an out. Tell him you think it might change your friendship dynamic if you cross that line. There is even a Seinfeld episode you can be watching to start the conversation. It’s better than critiquing his technique or offering him a bottle of Extenze.

@Zendo I meant I did not want you thinking I was saying something akin to “WHAT DO YOU MEAN CATHOLIC!? WHAT’S WRONG WITH CATHOLICS HUH!?”
I was raised catholic but where I live religion is not generally taken particularly seriously so I doubt I could understand the sentiments you’re expressing (my not being religious doesn’t assist matters either). In truth I initially thought you were intent on referring to an issue with the man having a foreskin, hahahahaha.

Definitely gay , lol

OK here’s the rundown: Sit down together, then ask him what’s bothering him (don’t ask IF something is bothering him, he’ll lie). Don’t let him cop out with “it’s nothing”. Talk about the problem, be sensitive and don’t humiliate him, it might even be a completely unrelated problem, something that’s just on his mind.

After that the problem should be gone. If it isn’t ask him flat out what’s wrong, while you’re still on the bed, don’t let time pass. It might get emotional but at least you know he’s gonna be honest about it.

Afterall if the problem is that he can’t maintain it when he wants to penetrate you it’s not impotence, it’s just a mental block.

Addendum: did you tell him about some past BF’s sexual achievements? does he know some of your exs?

@galileogirl I seriously don’t see a man turning down an offer for sex. I wouldn’t, unless the partner was incredibly revolting. Which i assume isn’t the case since they’ve been having sex several times without problems and this problem popped out recently

@Zendo I am but I don’t know about him, either way it’s nothing like that

@galileogirl I was tipsy, he wasn’t (and he didn’t liqour me up to get me in bed to avoid that discussion). We’ve talked about sex and neither one of us rejected the idea, even our friends are surprised it hasn’t happened before now. It’s possible though that because we’ve been friends for so long it’s hard for him to see me that way… good point.

@Thammuz >>“Afterall if the problem is that he can’t maintain it when he wants to penetrate you it’s not impotence, it’s just a mental block.” that makes me feel a lot better because that doesn’t mean it’s impossible, unfortunately it does mean I am (more likely than not) part of the reason.

oh- and @RareDenver gay is def not it but good try haha

Most likely he is still in love with someone else.

You say the problem is with insertion. Have you tried a hand job?

Interesting that nobody can imagine a guy turning down sex. Maybe none of you horndogs have ever had a friendship with a woman (or anyone) , Maybe he has brotherly feelings toward @sevenfourteen, of course that wouldn’t stop @Thammuz-warning to his sisters.

Why is it so important to @sevenfourteen. Do you live on a desert island and there are no other prospects? Or are you trying to prove something to yourself like you are irresistable or are you on a power trip? Both are signs of poor self esteem. Real friendship is more important than a roll in the hay-you don’t know what you’ve got til it’s gone. Wake up, kid.

He may be getting nervous and that could be causing the problem. I mean youve known each other for a long time and been good friends so maybe hes afriad he’ll fuck it up. Or maybe he wont be good enough for you. Even if he doesnt say these things he can still have the thought bouncing around in his subconscious and thats enough to it go limpy.

Have you tried any foreplay or do you go right for the goal? If not, i really suggest some foreplay to get him really worked up and wanting it more.

That and talk to him, really. I know its going to be awkward, but not as bad as if you guys just keep pretending it didnt happen.

GA @uberbatman
I’m not sure how experienced he (youguys) are, but don’t freak out or make it a big thing… it really might just be the nerves.

If you are wanting to pursue this relationship (romantically), I’d say be laid back about it, give it some more time, and it’ll probably work itself out.

Focus on physical pleasure. There are things you can do to each other that are very sensual and pleasant that do not require an erection. If you focus on them and on enjoying each other physically, and the problem is mental rather than physical, it will probably go away fairly quickly.

It’s also possible that the condom is causing problems for him, but that might be mental too—putting on a condom can be a very clinical act, and that disrupts the mood. If you do get to the point of talking to him about this, the thing to do in that case (it worked for me) is to get a super size box of condoms and incorporate them into sex play.

@galileogirl it’s not that we have to have sex and that I don’t enjoy our friendship. It has taken a year of us being a little more than friends for us to even get to sex and even still I’m hesitant because if anything goes wrong I’ve lost one of the best people in my life.

@uberbatman good point.

@cwilbur the condom never stood a chance, it’s at that point when it’s all over for him

Tell him to stop masturbating, between takes, simple really.

@galileogirl My nonexistent sister thanks you for the warning.

As for having a friendship with a woman i don’t see a conflict with wanting to have sex with her and being friends. Sex can be a way to show affection, not necessarily only the love you feel for a lifelong partner. I have several female friends but if it turns out one of them wants to have sex with me i wouldn’t say no, that’s for sure (providing i’m not committed at the moment, obviously).

@mammal That’s almost certainly not the problem. I can tell you from personal experience that chronic masturbation doesn’t make you impotent. It can make it harder to reach orgasm but certainly it doesn’t make it harder to get it up.

@sevenfourteen The condom might be the problem, i never had problems THAT big with them but @cwilbur is right, it’s a real moodkiller.

By the way has this situation been solved? i’ve been away for a while…

@Thammuz It’s about time that you guys got the mindset there are greater ramifications to unprotected sex than your mood.

@Thammuz – we’re actually together now, and nottttt very much. We talk about it all the time now, and the most I can say is that when I told him it was all in his head he agreed and said he couldn’t help his need for perfection. I’m away at school now so for the time being we connect in other ways but surprisingly the fact that we haven’t “officially” had sex (the closest we’ve gotten is with a semi which works….slightly) doesn’t affect the way I feel about him or our relationship- if anything it makes it stronger because through talking about it have made us closer and more trusting of one another (now I sound corny so I suppose I’ll stop)—thanks for asking

@galileogirl After two years of mandatory sex ed i’d have to say either “DUH?”, “No shit, Sherlock?” or “No fucking way, really?”.

Too bad i never talked about UNPROTECTED sex. The educated part of the population here in italy doesn’t have unprotected sex (as a general rule, there always are morons in every cathegory). First and foremost because it’s stupid (you know, babies, abortions, STDs… nasty shit), secondly because condoms are cheap and it’s really not a problem getting them so why not?

And by the way condoms work, if you don’t do it with someone dry as the sahara desert you’re safe. And if you do have that problem there is either lube or good old oral sex to solve it.

I never suggested that they didn’t use a condom, i simply said that, yeah, that could have been the reson why he lost his erection.
I personally do lose it partially when i put on a condom, but then i look at my gf and the problem’s gone. We’re all wired differently though and maybe that really is his problem.

That said if they stop using condoms she should either get on the pill or use some other contracceptive, but that’s obvious, i didn’t think it was necessary to state it. Afterall we ARE somewhat adults here.

@Thammuz Your words, not mine . . .

“The condom might be the problem, i never had problems THAT big with them but @cwilbur is right, it’s a real moodkiller.”

. . . DUH!

@galileogirl No, shit. It IS a moodkiler. That said i never said “you should stop using it”. as a matter of fact i didn’t give any advice since @cwilbur already gave the right one: “the thing to do in that case (it worked for me) is to get a super size box of condoms and incorporate them into sex play.”

And for the record, since when saying that you don’t like something equals suggesting not to use any form of it? condoms aren’t the only contraceptive in existence, for chrissakes! As a matter of fact my girlfriend and i generally don’t use them because she’s on the pill.

We use them only when we can’t rush to the bathroom to clean ourselves up to avoid making a mess on the bed (or wherever else we were doing it).

So please stop making shit up, you can read apparently so you know i never ever said that they should stop using condoms. I simply stated a true fact: condoms ARE moodkillers, expecially when it’s the guy who has to get up, search in his wallet, find it, open it and put it on. It’s a long operation which has nothing sexy about it and generally distracts you from what you were about to do.

And about that, @sevenfourteen: have you tried being you putting the condom on him instead of letting him do it?

He’s probably feeling a lot of pressure because you guys have talked about it so much and have so much history. So it could be a mental thing on his part, like he’s having doubts about whether he’s doing the right thing. Also, the moment of putting on the condom makes a lot of guys go soft- it’s a sudden drop in sensitivity with increased pressure to perform. If this is just a physical issue or performance anxiety for him, it should be easy enough for you to deal with. Tell him that you like him and don’t judge him and be patient. Engage in lots of foreplay (maybe some foreplay-only sessions), and after he puts the condom on continue to stimulate him to make him hard again. Until he can get it up, have him stimulate you in other ways.

@Haleth welcome to fluther. Lurve.

This sounds like a case for Dr. Viagra.

Buy a box, give it to him and see what developes.

The first time with a woman, for the man, can be certain failure and then no problems after that. With you, you guys have a history, and that can make it even more of a problem for him, regardless of his age. He should try Viagra, even at his age…to get him over “those embarrassing moments”.