It's been a long, long time coming...
January 12, 2014 11:13 PM   Subscribe

My relationship is great, with one small problem - no matter what my girlfriend and I try, I'm not having an orgasm. Oversharing details inside...

I'm a straight dude, mid-thirties and was a virgin before this relationship with really no dating history to speak of, although (unfortunately in retrospect) with a vigorous "death grip" masturbation habit. She's of similar age, and has a fairly short relationship history herself. We've been dating for going on four months now, and it's great. We spend every weekend (and a night or two between) snuggled up at my place - we're quite physically affectionate - and it's starting to feel like it could be something serious. She's super great; funny, kind, smart, really compatible values.

I've always been easily able to make her come, so that's great, but she hasn't been able to return the favour. Actual vaginal intercourse is difficult; I'm pretty overweight with a big belly and a shorter penis, so reverse cowgirl is the only position that works, and I frequently slip out. On top of that, I'm uncircumcised and my foreskin rolls back, exposing my super-sensitive head and causing me pain, so we can only do it with a condom; all I usually feel is a vague warm sensation.

When she tries oral/masturbation to get me off, it's pleasant for a while but eventually (after plenty of effort on her behalf - these sessions stretch towards an hour) I just kind of get numb, and it seems pretty clear I'm not going to climax. I have a hard time providing coherent feedback; I really enjoy what she's doing, but it's just not putting me over the edge.

I did knock off masturbation entirely for the first month or so, but I just got so horny I eventually gave in. I now masturbate and climax once or twice a week -- I had been doing it every day before we started dating.

We're starting to get frustrated -- especially her -- with the lack of progress. We do have pretty open communication about sex (she's laying next to me right now). Any ideas and suggestions would be great, thanks!
posted by Ed The Sock to Human Relations (30 answers total) 2 users marked this as a favorite

Masturbate together, or let her watch you masturbate, so that she can learn how you get off.
posted by parmanparman at 12:07 AM on January 13, 2014 [4 favorites]

You might also try masturbating to the point that you're about to orgasm, and then let her take over.
posted by MadamM at 12:19 AM on January 13, 2014 [1 favorite]

You are certainly welcome to work your own equipment while you kiss/make out with her....
and she can join in when you are ready.

Not every ejaculation needs to be vaginal.
Relax and have a good time!
posted by mdrew at 1:13 AM on January 13, 2014

I used to work in a sexual health clinic and what I was told was that the fit of a condom can have a big effect on what you can feel. Not just the size but the shape. Some are tapered at the end, some have extra room there. And, of course, some are extra thin or extra thick. You might want to try several different ones, and experiment with heating or cooling lubes for more sensation. Remember a little lube goes inside the condom for best results. Don't just put one on straight out of the wrapper.

You could also experiment with a weak stamina spray to try and cut down on the painful sensation during unprotected intercourse. I don't think that one is one of the weaker ones (in fact, I think it's quite strong), it's just an example. Most have lidocaine as the main active ingredient.

I don't know who the best sex toy supplier in Canada is or how their healthcare system works. Don't be afraid to speak frankly to either a reputable seller or your GP. Or to push your GP to refer you to a specialist if they can.
posted by K.P. at 1:45 AM on January 13, 2014 [3 favorites]

The suggestions about masturbating together are spot-on. And there are many other fine sex positions that could work for you, and it may help you to experiment with some of them. (Here are a few examples.) If you're not inside very deep and you keep slipping out, it could be that you're not getting as much friction as you need.

I think the combo of the position and the condom could be what's killing your coming. If you can arrange an alternate method of birth control, and you're both tested and healthy and all that, I'd say try ditching the rubbers.

As for the foreskin rolling back and causing you pain... I've never heard of that, ever. I wonder, are you fully erect when you're having sex? Because if a penis wasn't fully erect, then I can maybe imagine the foreskin doing what you're describing. But I really don't think a fully erect penis should be having that problem.

Finally... there is such a thing as telling a harmless white lie for the good of your relationship. Women can sometimes have a great sexual experience without coming, and sometimes they'll fake an orgasm anyway to make their partners feel good. And... men sometimes do the same thing. If you're having a great time but your girlfriend is getting freaked out about how you never come with her, you could always show her your O face and just tell her you came. Really, what's the harm?
posted by Ursula Hitler at 2:04 AM on January 13, 2014 [2 favorites]

Also nthing masturbating together as a great way for her to learn what you like, and vice versa.

I don't think faking it is in anyway helpful as it will not help either of you learn how to get there together, and it would probably upset her to find out at a later date that this thing you are trying to achieve together, the shared experience, didn't happen when she thought it did. I've experienced something similar and there were literal tears of joy and release when it finally happened, so don't deny that to either of you.

With regard to your head being so sensitive, are you using loads of lubricant? I mean, loads? That can really help. I know someone with a similar issue (though his doesn't sound as extreme) and he says lube helps a lot.

Finally, maybe try taking the pressure off the orgasm entirely for a while. Do you think you could both agree that you're not even going to try to come for a month, and that instead you are going to fully enjoy all the other great aspects of sex that you didn't have when you were masturbating to climax only? The touch, sounds, eye contact, intimacy, talking dirty to each other, all the other sensations that go along with good sex. It's really easy to lose your orgasm when you're putting all your efforts into attaining it, but maybe if you take that off the table for a while you'll relax and it'll happen in it's own time. Good luck!
posted by billiebee at 5:01 AM on January 13, 2014 [1 favorite]

I don't think this gets mentioned nearly enough: sex is a many splendid thing, and very rarely looks like it does in porn or movies. You don't have to come with PIV to prove you're having a good time. People with totally average experience, weight, equipment and jerk off routines all have failed to get there. If you never get to the point that she can do it for you, and you always need to take over? Seriously, that is OK.

You probably do want to give up the death grip, tho. Just to get the whole thing off of hard mode.
posted by Blisterlips at 5:40 AM on January 13, 2014 [3 favorites]

Having reviewed the professional literature in this area, ejaculatory incompetence is 80% a mental health problem. Dan Savage is a guy who writes advice columns and not a medical professional. I suggest a trip to a therapist and/or urologist or other reproductive health doctor.
posted by Ironmouth at 5:55 AM on January 13, 2014 [1 favorite]

I'm pretty overweight with a big belly and a shorter penis

Just how overweight are you? I ask this because a few years ago I weighed over 500lbs and had a VERY similar experience to you. If you're only 30-50lbs overweight it could be something else, but if you're 100+lbs overweight you could be having blood flow issues. Obviously if you're significantly overweight that's not going to change overnight, but you may want to start doing some light cardio work to improve your blood flow and circulation. If you're diabetic you may need to monitor your sugar levels prior to being intimate.

You don't mention it but do you take any medications by chance? Certain anti-anxiety/depressants can cause Anorgasmia, which is exactly what you're describing. I used to take a ton of medicine (ADD, anti-anxiety, HBP, diabetes, gout, blood thinner) and it caused all kinds of side-effects. Once I was able to cut out most of it a lot of the side-effects went away (thank g-d).

If I had to guess I'd say it's the "Death Grip" that's causing your issues. You don't explicitly mention it but I assume you are able to climax by masturbation, correct? If so, you may need to stop doing that for a LONG time to get your penis used to being stimulated by something other than your hand. You should probably also speak to your doctor(s) to see if there are any issues neurological or urological issues at play.

I think a lot of guys that weren't super sexually active during their young adulthood (16-30) have sensitivity issues as a result of the "Death Grip". Your partner is supportive so stopping the "self-love" for a while to get used to her might be what it takes to "reset" your sensitivity.
posted by playertobenamedlater at 6:07 AM on January 13, 2014 [2 favorites]

Response by poster: Thanks everyone for the helpful responses so far; a couple of quick clarifications:
- our primary sexual interface is manual and secondarily oral; vaginal is a once-in-a-while thing and I don't expect to orgasm from that, although I certainly wouldn't be upset if it happened.
- I have done some masturbation with her, although I've been more of a supporting role (and giving her arm a break)
- while I appreciate the idea of the little white lie, my inability to orgasm is the biggest issue in our relationship at this point, and a lie about this doesn't seem so little to me. Not to mention that it seems like it would be difficult to fake it when my dick is in her hand.

I wonder, are you fully erect when you're having sex?

Just how overweight are you?
100+ lbs.

You don't mention it but do you take any medications by chance?
I take a few; I've already asked my case pharmacist about them and he's noted that if I don't have a problem maintaining a physical erection, which I don't, that they shouldn't have any other effects on me.
posted by Ed The Sock at 6:30 AM on January 13, 2014

The resources suggested in this previous question may be helpful.
posted by Dip Flash at 6:31 AM on January 13, 2014

my inability to orgasm is the biggest issue in our relationship at this point

Lucky couple, if this is your biggest problem.

It's not the destination, it's the journey. As long as you're both having fun, don't worry about whether you come or not. Male orgasm is the game over state. If you don't come, you get to keep having sex! Win!

(Also, paradoxically, you might find that once you stop having that "jeez is it going to happen this time? It's bothering her that I haven't come, we've been going at it for an hour, maybe I can't, what if I never will, what's wrong with me" etc voice in the back of your head distracting you, you may not have the problem anymore.)

That said, if you're determined to make this be an issue, this is not helping you:

I'm uncircumcised and my foreskin rolls back, exposing my super-sensitive head and causing me pain, so we can only do it with a condom; all I usually feel is a vague warm sensation.

"A vague warm sensation" is perhaps not so much conducive to orgasm. A super-sensitive head, however, is. Try it without the condom, and if you're feeling pain, slow things down until it feels good again.
posted by ook at 6:47 AM on January 13, 2014

I've already asked my case pharmacist about them and he's noted that if I don't have a problem maintaining a physical erection, which I don't, that they shouldn't have any other effects on me.

I think it goes without saying that you'll want a second opinion on that.
posted by playertobenamedlater at 7:11 AM on January 13, 2014 [3 favorites]

If you're still using a death grip when you masturbate, STOP.
posted by Specklet at 7:21 AM on January 13, 2014 [1 favorite]

we can only do it with a condom; all I usually feel is a vague warm sensation

Put some lube _inside_ the condom: world of difference.
posted by Dr Dracator at 7:22 AM on January 13, 2014 [1 favorite]

my inability to orgasm is the biggest issue in our relationship at this point,

Why is it an issue?

You don't mention who is bugged by you not coming. Is it you or her? Does she feel that she's not doing her part or do you feel that sex sucks without the big "kaboom" or is it just a general feeling that it should be happening and isn't?

If you genuinely aren't enjoying yourself then that's one thing. If you like the sex and she likes the sex, but it's just not resulting in an orgasm, well, there are lots and lots of fun things that don't result in orgasms and they don't stop being fun things as a result. Bowling. Never results in an orgasm. Still a fun thing to do.

I'm a little slower out of the gate than the Lady Lurgi and, in the early stages, I frequently wouldn't come at all. She figured this meant that I wasn't enjoying myself. I assured her that I was having sex with an amazingly hot woman and, yes, I was most definitely enjoying myself.

Try varying your masturbation technique. Different locations and methods. Try using the other hand. One possibility is that your body is so used to coming one particular way that it just won't recognize the other ways as valid. Teach it.
posted by It's Never Lurgi at 7:27 AM on January 13, 2014 [2 favorites]

I'm also concerned by your girlfriend's lack of help and pressure in this situation. Perhaps she's not thinking it out and responding to the (not true) idea than men are always going to ejaculate every time. This isn't the case. She needs to be supportive and not putting the pressure you describe on you.
posted by Ironmouth at 7:43 AM on January 13, 2014

Sex is a physical activity and you have to train for it. (I am going to assume you have been screened for diabetes, medical conditions, etc.)

I would suggest you start with 10 minutes/day of crunches, planks, pushups, and general core stretching. Split it up into two or three sessions spread over the day, if necessary. Build up to 20 minutes/day over three months.

Likewise, I would suggest you start with 10 minutes/day of a core-focused cardio exercise. Swimming or erg machine if possible, but if your fitness level does not allow then try an elliptical machine. If you can't sustain, stop to catch your breath but use a continuous countdown and try to keep moving the largest percentage of the time that you can. After three months, aim to be up to 20 minutes/day. Once you can go the full time at a continuous steady effort, then work on starting slow and building the intensity until you finish at peak exertion.

Finally, I would suggest doing kegels. Start with 20/day. Split into different sessions over the day, if necessary. Practice urination control when possible. Build up to 100 kegels/day over three months.

In summary, people who are inexperienced or have been inactive don't realize that sex is very physically demanding. I'm not talking about being a bedroom hero. I am just saying for normal Monday night lovemaking with your significant other.
posted by 99percentfake at 7:45 AM on January 13, 2014 [2 favorites]

Response by poster: You don't mention who is bugged by you not coming. Is it you or her? Does she feel that she's not doing her part or do you feel that sex sucks without the big "kaboom" or is it just a general feeling that it should be happening and isn't?

It's more of a problem for her; she's admitted that this is making her feel inadequate. Last night, sex ended in (her) tears of frustration. (I posted because I'm a MeFite and she isn't.) She may be feeling some guilt, since I get her off easily and she can't return the favour. I've been trying to provide better feedback, and she's been very game about trying anything I can come up with (although that isn't a lot, since I've never had an orgasm with a partner, so I have limited scope for advice). We've been trying to keep the pressure as low as possible; our mantra is "it'll happen". But, you know, it's been four months of regular attempts and it's getting harder to keep spirits up and be confident that it will happen at some point.
posted by Ed The Sock at 8:05 AM on January 13, 2014 [1 favorite]

This is maybe a little more out there than you're willing to go, but I know of at least a few people who've gotten past this (where "this" is "former deathgrip on penis" or "obsession with watching porn to get off") with butt play, either on its own or in conjunction with a blow job or whatever. It's a novel enough sensation for many guys that it...I dunno, presses buttons that penis stimulation alone does not.
posted by MeghanC at 8:08 AM on January 13, 2014

I am of the opinion that an orgasm is an orgasm and if both parties are having fun having sex, then if it comes from actual intercourse great, or if it comes from you jerking off while she plays with your balls also great. I say that just so you know that I think this is less of a problem than you both think. However if your gf is bothered by it, it could well just be her thinking you don't find her sexually attractive so you might want to show her that in other ways, when you are eating her out make sure she knows you find it the hottest thing ever, be intimate and affectionate in non sexual ways. Even if you think you are doing it a lot, dial that shit up to 11 and keep going. As a generalization lot of sexual enjoyment for women comes from feeling sexually attractive, that the guy you are with wants because you are the hottest hotty ever, you can make her feel like that without you orgasming.

If it's you stressing out, then just a suggestion, as you say that not masturbating makes you super horny, which is kind of the point you want to make yourself so horny that stimulus that wouldn't normally work will set you off. The point you are feeling super horny you can't think is when you should be having intercourse. Hell make yourself even more horny, masturbate (no death grip use a flesh light or something to control the pressure) until you almost come then stop, do this once or twice a day for a week or so and you'll come if she even looks at your penis funny (also according to guys I've done this with the orgasm when it finally comes is mindblowing). Being horny won't kill you.

Also look into better fitting condoms, they shouldn't be sliding around on you.

Good luck with it all, and talk about this with each other, but not during or just after events, but in the cold light of day. Sit down, hold hands and talk about what she wants and you want, and work out ways, the 2 of you together can reach that goal.
posted by wwax at 8:21 AM on January 13, 2014 [2 favorites]

When I first started having sex, I couldn't get off via a partner's efforts, and I found the more urgently my partner wanted me to come, the less fun sex was. I don't think pressure helps orgasm for most people.

I'm now pretty easily able to reach orgasm, but I'm with a guy who has a hard time getting off, so my orgasms feature a lot more in our sexytimes than his do. More than half the time he comes when we're playing, he's getting himself off with his hand while I play with his nipples or get myself off while he watches.

If you are genuinely okay with sometimes not coming, this is something you could work on as a couple: being okay with the fact that different bodies are different and that sex is fun and awesome and feels good whether or not an orgasm is involved.
posted by spindrifter at 8:40 AM on January 13, 2014 [1 favorite]

I just had a lot to say about blow jobs ten days ago. Specifically, the asker had mentioned that "For my part, it feels good at first but gets repetitive and I go a little numb." And you seem to be reporting the same issue here as that person.

So my advice there stands for you. Porn probably won't fix this, as porn is made up of unrealistic expectations/lighting/contortions/etc. Talking might, both inside and outside of the bedroom. Definitely for exploring what sensations you enjoy in the moment. If she's doing the same thing over and over for an hour and you are getting numb, then that is just as much on you as her. Because if you're not having a very good time, she needs to know about it so she can change things up. So vocalize your preferences.

Outside the bedroom, figuring out the true real reason behind why she is upset by this, and addressing the actual true real reason might help. This might mean therapy for her. It might mean therapy for you both together. Sex can be a proxy for lots and lots of other emotional stuff. Many women are taught (subtly or not) that our sex lives define our value. This would make her "failure" to bring you to orgasm some potentially raw stuff. Lots of men have their value wrapped up in sex in some ways also, but more about just getting laid than about getting anyone to an orgasm. There's a reason it's a trope that the guy orgasms, rolls over, and falls asleep, leaving the woman unsatisfied and lonely. You may be subtly broadcasting messages that you aren't aware of holding.

Sooooo. More cuddling. More specifically and explicitly not orgasm focused sexy time. More talking about sex and everything else. More time spent together just enjoying each other, without any kind of sex. Maybe take a walk each evening, starting for for twenty minutes (which hey, also has health benefits galore!) and working up to thirty minutes. Walking makes it so much easier to talk about difficult things. Walking means that you're not face to face with the person, and there's not need to fidget. Walking gets things flowing, and words are included in that. When you get back to the house, you have the perfect opportunity to enjoy some gentle fooling around in the shower!

And, because this has not been mentioned before, alcohol and cigarettes, as well as illicit drugs like cocaine, can impact ability to orgasm. You don't report using any of these things, but if you are, cut back on them/quit. Drink more water. Not gallons and gallons of it. But between lunch and dinner, sneak in another glass each day.
posted by bilabial at 8:54 AM on January 13, 2014 [1 favorite]

Teach her the "death grip"?
posted by sawdustbear at 11:28 AM on January 13, 2014

My ex was very round with a short penis, and also incredibly sensitive inside his foreskin (I think something surgical should probably have been done when he was young - he disliked pulling it back at all, even for washing, I think it was just way too tight and too late in life to fix that although not sure and he didn't want to discuss). The best luck we had was with woman on top (she can put pillows on either side if she has shorter legs) and moving very quickly up and down while the man thrusts up a little, no condom needed, maybe a little lube sometimes but too much is definitely bad. I think that is the only way he ever came with me. You could give it a try. Your partner might need to work on her thigh muscles though, so might only be able to do it for a very short while to start, it does get easier fairly quickly though. You should also try to relax and focus on the sensations, close eyes if needed and breathe slowly, if you are constantly fussing with things then much less chance of coming.
posted by meepmeow at 12:24 PM on January 13, 2014

One part of this seems to be that your partner feels responsible for whether or not you have an orgasm, which is putting a lot of pressure on both of you. So she is feeling inadequate as a woman. You can help by giving her positive assurance that you find her sexy and attractive. Let her know when she does something that turns you on. General statements are nice but specific ones are even better. So during sex, if you like her body feels or if something she does feels nice, tell her (with words or sounds but sometimes words are clearer - "mmm, your breasts feel so nice and soft and firm" or "wow, that touch is making my whole body tingle")

Also when you masturbate, is having her there better than being alone? How? Let her know.

Also, as you pay more attention to what turns you on (so you can tell her) you might find more ideas of new things to try, so a double win.
posted by metahawk at 12:28 PM on January 13, 2014

There's a lot of good advice upthread, but something that hasn't been mentioned here is that you can also try things that make you more likely to be aroused; marijuana works for many people.
posted by klangklangston at 5:34 PM on January 13, 2014

Just jumped in here to n-th lube for the foreskin issue. I have a similiar issue, and a large amount of lube (Astroglide specifically, KY doesn't do it for me) helps a lot.

And as others mentioned, relax a little.
posted by pyro979 at 6:49 PM on January 13, 2014

It's more of a problem for her; she's admitted that this is making her feel inadequate. Last night, sex ended in (her) tears of frustration.

So, the problem is not about your orgasm but about how she feels about it.

I'm not sure if a couple's therapist would be helpful here or not. There is no need for her to feel inadequate. Many men orgasm with difficulty, after a long time, or only in very specific ways, or not at all; it's not about her.

If the two of you can find a way to have fun in the bedroom (or wherever) that isn't goal oriented towards your having an orgasm that might be helpful.

Depending on her views about sex and what it means to her she might have to some work to do to change some of her thoughts before she sees this as something that does not mean she is "inadequate", and she has to be willing to change.

Also, try different techniques for masturbation and take the death grip out of the rotation.
posted by yohko at 11:34 PM on January 13, 2014

I have trouble orgasming with a partner sometimes, and it's really nice to masturbate almost all the way and finish with him, either with intercourse or with him just kissing or touching me while I come (and cuddling after).

You can masturbate almost all the way then she can finish with a blowjob. I think if you get used to this routine, either with sex or bj, then you can eventually shift the amount of time you spend with her to a greater and greater proportion of the total experience.

Plus with this technique, you do most of the work and she gets to enjoy the ending. So no more sore arms for her. The key is to masturbate until you are just ~dying~ to come, then start having partner sex at that point.

When I do this, it will actually take a few more minutes than expected when the partner sex starts, because I get distracted during the transition. And sometimes I still can't have an orgasm which is frustrating. But lots of times, I can, and it's a good way to enjoy sex together.
posted by htid at 8:44 PM on January 14, 2014

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