(NSFW) What is the best way to handle this delicate situation?

Be honest and gentle with him. He’s not going to have a clue about your needs if he’s inexperienced.

Wow. It sounds like he needs a good chat or two with an experienced male friend. From how you’ve described him, almost any chat with you about the subject(s) will be a disaster. Not that that is your problem, of course, but (drum roll for ridiculously cliched expression) it is what it is.

To you it is how and when you will ask/tell him this:
Next time the both of you are going to be intimate he has to keep one thing in mind: today he will NOT reach orgasm/he does NOT WANT to reach orgasm.
He may enjoy the play, of course, but coming is out of the question.
If that possibly means no penetration; no penetration.
It is almost all about you, he can enjoy giving you joy.

Be honest with him and tell him in a respectful way that you are not being satisfied and that he should try to do better. Dont say anything hurtful to him, I know you are upset and angry with him but there is nothing that you can do to him worse than hurt his pride as a man and that could affect him later in his life. Try to give him some tips of what you like sexually and also try to encourage him by speaking to him as he gives you foreplay. Play with his mind a little and boost his ego by telling him that you are turning him on and you like what he does to you. When you boost his ego, he will be encouraged to do better. Also, ask him why he comes prematurely. After he gives you his answer tell him some good ways to improve. Try not to make him feel to nervous around you.

Tell him what to do. Tell him you want him to touch you here. Now there. Use his lips on your breasts. Now kiss your neck. Longer. Spend more time on your neck. In other words, take charge, but not like you’re taking charge, just like you’re telling him what you like.

I think most guys would be grateful to know what you like because most want to please you. And of course, if he doesn’t want to please you, that tells you something, doesn’t it?

He’s new to this and he doesn’t know what he’s doing and he may not even know that you experience pleasure differently. It’s hard to imagine someone can grow up in this day and age and not know about premature ejaculation, but I suppose it’s possible.

Do this in a non-judgmental way. When does something that feels good, let him know. But don’t be afraid to ask for what you want or just tell him what you want. I find it pretty sexy when a woman tells me what she likes. Of course, it’s more sexy when it’s something I want to do anyway, but hey, my wife gets off on back rubs, so why shouldn’t I please her by massaging her where it is all knotted up?

He probably will enjoy pleasing you, too. So think of it as giving him an opportunity to please you. Tell him what you want him to do, very specifically. Let him know you enjoy it when he hits the right spot.

“Let’s play a game…. for the next hour, you have to do exactly what I say. And then after that, I’ll do exactly what you say. Interested?”

If he can’t hold it, how about a second round after a 10 minute break? I guarantee he will last much longer.
You might even take care of round 1 in the shower. That way you both will be squeaky clean and can fully enjoy the event.
Don’t let this issue stand between you and good relationship. He’s not doing it on purpose. Don’t quit after the first one. Plan on round 2—- or 3! You’ll both appreciate it.
Talk with him.

Just tell him, openly, honestly, and understandingly… exactly what you just told us. Tell him exactly what you want him to do, be explicit, and be patient. Assure him that you know he has the “equipment” and ability to do the job, he just needs to be shown how to do it.

@stardust LuckyGuy had the key point. He’s not doing it on purpose. Most men want to be great lovers. Some just don’t know how.

I want to be open and honest with him but he’s quite sensitive so I want to make sure I do it in such a way that he doesn’t feel like **** afterwards.
Should I tell him I want him to try other things/explore more, etc?
I am surprised as we’re both mid-late 20’s but I don’t want to judge either.

@stardust I would have liked that when I first started out.

Rather than give directions, I’d start by asking questions about sexual experiences he’s had and how he feels about sex. Some people (men and women) are concerned about germs and don’t really like to kiss, for instance. How did he learn about sex when he was a kid? (We all have stories about that!) Does he like to be touched? Does he enjoy sensual touching, not just of people but sensual fabrics like velvet. In fact, talking about the senses and which are most important to him (and you). I think you get my drift. Ask. Don’t give orders. Suggest trying this or that or illustrate what you are talking about.

Little known fact…. if you dated a guy without a prostate you would not have this problem. I heard they last forever. ;-)

If I were the XX chromosome holder in this situation I would let him rest for 2 minutes and then put an appropriate part of my body within a tongue’s length of his mouth. Ten minutes later you can start playing with him so he has time to fully reset and go again.

They tell young guys to think of other things to prevent premature ejaculation. “Think of
baseball. Think of your mother. Think of blah blah blah” I say BS! Get rid of that first shot right away. Take care of the woman while you reset. Then go at it a second time so you can be thinking of her and how to make the experience great for both parties.

@LuckyGuy I beg to differ a bit. We don’t know how inexperienced or repressed this guy is. We don’t really know what his issues are. It’s not just a physical problem; there’s a learning curve. He may not even know that women are supposed to be pleased.

@janbb I sure hope that is not the case. I assumed it was just a combination of inexperience and embarrassment. I think a discussion, after some play, is in order.

What made you not say anything both times? Were you embarrassed, self-conscious, or unsure of what to say? The longer you wait, the harder it will be for both of you..

With the information available today, I am surprised that even someone with little or no on-the-job training didn’t notice.

Personally, I would not wait until we were about to try again. I would choose a time and place where we both seemed to fell comfortable and simply start talking.

And also personally, I have always felt that the most important sexual organ was the brain.

Get him a book on how to pleasure a woman as a gift. Give it to him not when you are having sex, but at a different time. Look him in the eyes and say, gently but firmly, “You need to read this.”

@marinelife You missed the part where she said he was sensitive, didn’t you?

@6rant6 I don’t think telling him something gently but firmly has anything to do with sensitive. If he is sensitive, he will pick up on the need for improvement. Giving him a book gives him concrete help.

If he does it again I would just start masturbating in front of him and if he asks what your doing then tell him you need to get off too…

@LuckyGuy You’re right. I think he felt very embarrassed that he finished so quickly. He apologised.
@gailcalled The second time I spoke up. Admittedly, I was trying to tip-toe and so wasn’t as clear as I would’ve liked. I told him I think we should spend more time figuring out what works for each other. He was embarrassed so I left it at that.
@creative1 Yes, if he does it again I nearly would do that. Honestly, if it carries on this way I’m not sure the relationship would last long.

@stardust Try Nancy Friday’s book, Women on Top. It’s what women want. It’s an interesting if a little dated perspective. Give it to him to read.

Is it really that complicated? He is not “your kind of guy”. Or vice versa. Just tell him the two of you don’t have enough in commen to invest a lot in the relationship. You don’t have to be shitty about it. Just say it. Sort of like firing an employee that doesn’t work out.

Since he doesn’t have much relationship experience, he’s probably just about ready to burst at the thought that he’s actually fucking.

I would tell him precisely how you feel about him.
You need to let him know how you felt after your encounters. Most likely he has no clue.

He may need a book, or quite frankly just a good instructional Internet site (not porn). I’d say flat out, “I like to be pleased like this” and show him an example.

He may need to learn how to breathe and be patient. Yoga & meditation might help.

If you’re seriously interested in him, this may take some time & patience on your end, too.

I agree with most on here to first talk to him at a time when your not going to have sex. Some place where both of you are relaxed and just start talking,openly about sex,what he likes or what he has done before,tell him what you like,what you have experienced before.(dont say who or what,nothing like that) If you talk to him openly about sex and all you know and like,he just might open up to you and talk. Some people are shy or taught that sex is dirty. I have never experienced anyting like this but simillar. My soon to be husband who was 42 when I met him,3 years ago,he had experience but his ex didnt believe in play an touching kissing all the good stuff,and as soon as he found out that I was a very open sexual person,he was relaxed and the real him come out. We have a Great sex life, it is still hard for me to believe someone that age hadnt experienced what I call “real sex”. He didnt need any teaching just knowing it was “ok” and “not dirty” to do other things,like touching kissing,playing. He always wanted to please a woman but never had the chance due to his ex had no interest she said “that’s Dirty”. And I also agree with LuckyGuy,that if he is the type what gets so excited and cant hold off to do anything,then get the first one out of the way,like the shower idea,then afterr a few minutes start on round 2,who knows maybe even 3. We dont know how inexperienced he is or way,but if your open hopefufly he will open up to you,an please try to not embaress him,or hurt his ego,that is the worst thing you can do. If he is very inexperienced he will be pleased with all you have to teach him and then some. Dont be rude but if he isnt as sexual as you are after you try talking showing etc,then maybe your relationship wont work. If two people are not on the same sexual level,it usually will not work out. I wish you all the luck,and I hope all works out for you both.

You can get him books and if you have the patience, you could teach this guy exactly what you like but unless he takes some initiative, I doubt you will be happy having to be the one to do all the work.
There is no way I would want to always have to tell a guy what to do to pleasure me. I don’t see how that would be much fun for him either. Telling him what he is doing, do it over here, or do it like this drives you wild is a lot different than telling him each time specifically what he has to do to drive you wild.

This is tough. I know how hard it is to find someone you can relate to and connect with on a deep level. It seems this guy has a lot going for him and that you have a good relationship. so, at least so far the sex has been very disappointing. It seems that this is due to inexperience and not insensitivity. If so, there is hope.

I wouldn’t want to have to instruct a man how to make love, but that is me. Maybe you are more patient. It’s very possible that he was nervous and just a little quick on the trigger. If your feelings are strong otherwise and your relationship good you can work things out. I think. But I am not sure. I have experienced cases of pernicious premature ejaculation and it is extremely frustrating. I cannot say that I was brave enough to talk about it. I always thought that the guy would be so put off by my negative appraisal, however delicately put, that it would put the kibash on the whole relationship. Since you say that he’s sensitive it’s hard to say…
It’s very possible that with time and a greater comfort level and more communication you can work things out so that you are more satisfied. If not, it may be worth it to seek outside counseling for the premature ejaculation. With the right efforts it can be corrected. But in my experience, it does not just correct itself. A man needs to be aware of his body responses and learn how to control it and withhold. All the sensitve foreplay in the world cannot make up for a premature ejaculation.. But that is just my opinion.

He’s not that experienced. That is a good thing, IMO. Don’t expect him to be a mind reader. The only thing on his mind is how embarrassed he was that he came so quickly. You have the power to easily fix that. Rather than saying “That’s OK” and secretly fretting about it, fix it. With the biggest smile you can muster, wipe him off and say, “Great! The next one will take a lot longer! Mmmmm.” And then sit on his face while you are waiting. He’ll be ready to go in 10 minutes – about the same time as you. They you can both fully enjoy it.
You won’t have to tell him what to do every time. He’ll figure it out.

Honestly, would you rather he had practiced with 100 women before you and was a skillful player?

I dunno @LuckyGuy… she sits on his face, she may sufficate him. Poor fella won’t know what to do : (

Then she needs to tell him once.

You know what I’m talking about. Forget about the first one and concentrate on the 2nd and 3rd ones. They are the best! They are the ones that make a memorable evening!

I don’t know how “honest ” it is to say it was “grest” when a guy is not that great in bed. Most guys, as far as I have known, will take that at face value and assume you mean it. Why shouldn’t they? Do they think you have any reason to lie to them? Do they realize that you understand the fragile state of their male ego? No, mostly they do not. If you say they are “great” they think they are. I am all for being understanding but you cannot start off an honest communication by bullshitting someone that it was “great” when it was anything but.. Sorry, but it won’t get better by itself.

@LuckyGuy You’re assuming his is up for a round two or three. They’ve done it twice, he was embarrassed both times, he didn’t participate much in foreplay, and made no effort either time to pleasure her…
I would really pay close attention to his reaction when you bring the issue up.

How old is this guy @Stardust?

While waiting to hear how old he is, I would say I agree with @EnchantingEla. Being sensitive shouldn’t preclude him from receiving honest feedback. If he is too sensitive to hear that things aren’t working and he needs to do that to help improve things, he isn’t worthy of your time and effort. I sincerely hope that isn’t the case though.

I would suggest talking to him when there is no sex going on or likely to happen. Go for a walk and be honest. Tell him it wasn’t great the first couple of times but that you like and care about him enough to want to work on things and then you can bring in suggestions about showing him how to pleasure you, allowing him to climax once and then going for a second time etc. What about suggesting going to the bookshop and choosing some books together? This is a chance to learn about each other (he can teach you as much as you teach him). Part of the joy of a new relationship is the exploration.

Yes protect his feelings and ego, but not to the point that you are prolonging either your agony or avoiding ending things because he just isn’t hearing or isn’t willing to hear.

@Earthgirl i agree with you. In my statement above I did not mean to use the word “great” in reference to grading for his performance. It was meant to show that “It’s good we got that first one of of the way today. Now let’s get on to the real activity.” It was a poor choice of sentence structure.

@EnchantingEla Yes, I am assuming he is up for it. Obviously I don’t know the guy. but it seems that he is young, inexperienced and quick on the trigger. Good raw material to work with.
He’ll be up for it – if he’s not chastised or embarrassed.

@Earthgirl He is 26. Thanks for that and all of the sound advice. I’ve not been in this situation before, i.e. in a relationship with someone so inexperienced :/

Good luck @stardust. To me, this is a delicate subject to broach. I hope all goes well : )

@LuckyGuy Unlike yourself, he doesn’t sound very gung-ho nor very animated. He is 26 and inexperienced. You’re basically talking about training the guy from scratch (at 26!) and that’s fine if that’s what you want and have the patience for. I personally don’t. But then again, my days of teaching men how to roll are long gone. I want a man who at least has some clue as to how to please a woman, but I would never embarrass or chastise a man if he didn’t.

(And I can’t imagine “sitting on the face” of a guy who doesn’t have a clue that a woman wants pleasure too. What if he threw you off? He needs some education first.)

I’m not feeling too enthused about educating a grown man about sex :/ Why?

@stardust I think that’s normal. He should be figuring it out himself. But if he’s worth the effort outside of the bedroom maybe it’s worth teaching him?

@stardust A lot of people have major hangups when it comes to sex. They think it just happens. It doesn’t. It takes some learning and work. The fun part is when you figure out how to really please your partner, they’re always ready for more. :)

Maybe you’re not too enthused because you are a grown woman, you’re more sexually aware of your body. Only you can decide on the importance of sex in your relationship. Some people say it’s not important and that’s fine for them. For me it is important. Is it the most important thing in a relationship? No, but it does matter. I need that level of intimacy and self expression. I need the bond that comes from sharing sexually.
I think teaching a man ways to please me would not be an asset but more of a hindrance and would take away a certain sense of personal expression. edited in: IMO Teaching is not the same as letting a partner know or showing them what you like/enjoy sexually.

@Adirondackwannabe A lot of people may have hang-ups, but I don’t believe major hang-ups are a partners responsibility to figure out, sort out and overcome. That’s just my take on it.

We were all naive lovers at one point. It seems me the best part is sharing discovery. Who knows. This guy could turn out to be a real perv given half a chance.

I think it really depends on how receptive he is when the subject is addressed.

@6rant6 One of the best parts is sharing and discovering each other .Educating someone who is 26 just doesn’t sound right to me. The way I see it, she will the one sharing and he discovering. I wouldn’t do it but I’m not 26 either ; )

@EnchantingEla Speaking for myself, there was a time (well after 26) when I had occasion to go, “You mean it’s okay to do that? Yowza!” And more than once.

@EnchantingEla I agree. Sex is very important to me in a relationship. The issue of him just looking after himself is extremely frustrating for me as it makes me feel like some sort of “vessel”, for want of a better word, for his fun.
We’re supposed to be spending the weekend together and the thoughts of going through a 60 second fumble just doesn’t appeal to me. Naturally
I could try to broach the subject beforehand? I’m conscious of demanding something of him, but at the same time, we’re not 16.

@stardust I think you might as well just talk about it with him. You don’t want to stay with him if sex is important to you and he does not want to learn to please you. Run it up the flagpole and see what salutes and for how long. Sexual incompatibility is a relationship killer.

@janbb Thank you. I’m going to talk to him.

Best of luck!

Good luck @stardust. Nothing to lose by trying and you will soon know if he is open to improving or not. I hope it works out.

stardust I agree with janbb‘s advice.
You won’t be happy ultimately if the sex doesn’t improve, yet you need to give him a fair chance because it seems he has a lot going for him and let’s face it, it’s not easy to find a good guy. I might begin the talk by just not too seriously, a little offhandedly asking him if he was nervous the last itime he made love to you. You could even be a little flirty about it, then he will more likely feel comfortable admitting it if he was. (Did he seem embarrassed to have come so fast when it happened or pleased with himself?)

If he hasn’t been in many realationships it’s very possible that it was so much excitement that he couldn’t contain himself (lol, no pun intended) If that’s the case, making him feel more at ease, not making a big deal out of it, and letting him know that slow is good, should help matters. Encourage him rather than teach him. Tell him what feels good. If he’s too rough or too fast, keep giving him gentle reminders. This will work if you get your points across before the whole bedroom experience starts. If he doesn’t seem to know what to do, or he’s not doing what you want him to your can guide him non-verbally with your hands. I know it takes some of the magic out of it, but at least it’s better than having to tell him what to do and no one likes to be given a step by step action plan!

Does he come from a strict religious upbringing ? Those hangups can be hard to reverse or overcome but with trust and respect and hopefully love they can be.

I just noticed I typed loose instead of lose. OMG…

@Bellatrix We caught the Freudian slip.:)

lol@Freudian… absolutely it was. And it is gone.

@Bellatrix You’re a good sport. I cringed a little after I sent that. :)

LuckyGuy lol, I almost wrote worried Understood. Sometimes one ill chosen word can throw off your meaning or be given too much emphasis. I didn’t mean to do that. It’s just that women are often trained to do everything they can to mollycoddle the male ego and not to ask for what they want and need themselves. Too much selflessness is so bad!!! It leads to so much resentment and in the end analysis, the relationship suffers. Honesty can and should include kindness, but sometimes there’s just no easy, painless way to say it.