Help! I need sex advice!

A couple sitting together on a wall

Ok, let’s start with the beginning. I am a straight woman dating a bisexual man. We have a good monogamous relationship & we love each other very much & hope to one day to be married. But there is a fluke in our sex life.

We have been dating for over three, almost four, months now and the problem is we haven’t actually HAD sex yet. It’s not like we haven’t tried. We have. But for reasons we can’t understand one of our biggest problems is we can’t keep him hard long enough for him to put it in.

Our second biggest problem is the few times we have been able to keep him up we, for some reason, can’t get him in or can’t find the hold.

The third problem is the even fewer times (like so few I can count them on one hand) that we’ve been able to get him to stick it in we either can’t keep it in to do anything with it or it goes limp again & we can’t do anything with it. We’re not sure why this is.

At first he thought maybe he was gay. But that scenario doesn’t fit. He’s been with a woman before and had no problems then and although he does enjoy gay porn he also enjoys straight porn, lesbian porn, and a whole slew of other porn and while he does enjoy cock he also enjoys pussy. So him being gay doesn’t fit. Then he thought maybe he just wasn’t attracted to me. But that doesn’t fit either. I can get him up easily. He even gets hard when we kiss. He tells me all the time how beautiful he thinks I am. When he masturbates he gets off thinking about fucking me. He enjoys sucking my breasts and eating me out and he tells me multiple times a day how much he loves me. So there has to be attraction to me somewhere or I wouldn’t even be able to get him up. Then we thought that maybe it’s because he hadn’t actually had sex with anyone (man or woman) for thirteen years and even then it hadn’t been very much so it’ll just take time. But it’s been almost four months! Then he thought that maybe he was just too small, but that’s not true. He’s actually of average size and while I have had bigger I have also had smaller and have never had this problem before. Then we thought it might be erectile dysfunction. But he gets it up and keeps it up fine while masturbating, which he does a lot of.

He wants to penetrate me, he gets hard thinking about it, and I want him to too. I want us to get to the point of getting him to cum inside me. He has made me orgasm quite a few times by fingering me, but it’s not the same and I feel bad because I have only been able to make him cum twice. The first time being on our third month anniversary thanks to a handjob and a ton of baby oil. The second being just a few hours before I wrote this thanks to another handjob and him getting off on fingering me. But still, we both want the one thing the universe won’t seem to let us have. Can anyone out there help me with this problem and tell me how to resolve our issues so we can take our relationship to the next level?

7 thoughts on “Help! I need sex advice!

  • Hmm. Have you blown him?

    It’s really hard to say what’s going on here… Men’s brains tend to be really, really straightforward, but we sometimes make up for it by having really complicated controls over our cocks.

    One possibility, though, and I’ll just throw this out there… If he has the feeling that you’re squicked out by his cock, because you tell him you want him in you, but you’re less eager or it in an all-consuming way than, for example, his previous cock-hungry boy lovers have been, then it could be that he’s projecting revulsion onto you, even if that’s not what you’re communicating or trying to communicate to him, and if he’s not especially sadistic, that might kill his physical desire to put it in you, even if you and he both desperately want that, on some intellectual level.

    And then, of course, comes the stress, and the wondering, and the disappointment, and the self-recriminations, even if he never lets much of it show to you.

    I’d suggest that the way forward would be to enjoy his cock without having a specific goal in mind. Just, y’know, nuzzle it and kiss it sometimes, and maybe purr a little about how sweet it is, but don’t go too far with that. Just let him know that you like it. Maybe fetishize it a little. Rub it on your cheek, whatever. Let Mr Willy know that it’s an object of desire in itself, rather than as a tool for fucking you.

    Then, at your own pace, on the night or after a few days, move on to oral.

    Again, the goal is to convince the animal part of his brain that controls his hydraulics that you love his cock, that you really, really love it. That you want to feel it, touch it, lick it (and, yes, eventually fuck it) for what it is.

    This all may be enough to break down the barrier. Or this all may be exactly what you’re doing and exactly how life is between you both already – again, it’s hard to tell from a post like this.

    But this is a possible way through.

  • Also – dude needs to stop masturbating. If he keeps his hands off of it for a week, I expect he’ll be nailing you to the wall at the next opportunity.

  • Honestly, in a situation such as this, it would seem sensible to talk to his GP, to rule out any physical issues, and also ask for a referral to a therapist who specialises in sexual issues.
    The GP could prescribe Viagra, which would certainly help with the ‘staying hard’ issue. The therapist could help work on any psychological issues that are getting in the way.
    This is by far the most sensible course of action – we can say ‘try this’ or ‘try that’, but we are not professionals. Get advice from people who know what they are talking about. x

  • ” Then we thought that maybe it’s because he hadn’t actually had sex with anyone (man or woman) for thirteen years.”

    That is a LONG time not to have penetrative sex I’m not at all surprised he has no problem masturbating to orgasm but has problems penetrating you.

    You don’t mention sucking his cock. This is interesting because it is a way to ease him back into the act and sensation of being engulfed.

    My advice is that the pressure to perform is probably scaring the shit out of him. Just tell him – that’s it, no intercourse. Then play around with oral sex and other forms of ‘engulfing, – holding him between your thighs, your breasts, your buttocks. Oil helps a lot and feels great. And, I’m pretty sure on one of the closed-thigh occasions, things will eventually move along nicely.

    Just stop making it an issue. There’s so much good sex to be had that doesn’t include vaginal intercourse.

    Hope this works for you. Good luck to both of you.

  • Sorry, for crowding again, but I would also have a serious discussion about why he didn’t have sex for 13 years.

  • I agree here, stop focusin for now on the intercourse, each time it’s tried and ‘failed’ is a disappointment to you both and psychologically speaking this isn’t gong to help matters at all. I think I’d try gettin him to hold off the masterbatinh and you both just concentrating for a while on fore play, blow jobs just goin back to square one and enjoying each other again. 13 years is a long time without any sex I’m guessing you’ve discussed his reasons behind that? Not any of our business but may be something there . My husband gets up easily but can lose his erection pretty quickly no matter how turned on he is or how much he wants me, we’ve found cock rings to really help, they stretch can be reused until you notice wear and really do work in helping the man. They’re not fool proof though but it’s worth a try when the time comes.
    Also consider a visit to your GP could be physical could be psychological either way someone out there can help you. God luck Hx

  • Gosh – there’s a lot going on here. But the following is what particularly struck me.

    First of all, as RG says, 13 years IS a long time not to have sex. Have you asked him to masturbate in front of you? Because after 13 years he may very well be in quite a fixed masturbation routine. Maybe he’s a death-grip masturbator, in which case he may need to quit wanking for a while and retrain his dick to enjoy a variety of sensations and pressures.

    Maybe penetrative sex just isn’t his thing. Despite what he says, maybe he’s just too shy to tell you that he prefers oral sex and handjobs and that’s just how his sexuality works – it has only been three months! Either way it might be worth rethinking how you consider sex. “Oral Sex” has “sex” as its surname for a reason. It’s all sex. And people have preferences.

    The other thing is that it sounds like after three months you are treating this relationship as something really serious. It’s really not a long time, and yet you “love each other very much”? That’s a lot of pressure. Three months is not very long to get to know someone. You might want to ease off on the wedding plans and treat this as it is: a young relationship still finding its footing. Explore, play, and don’t treat the fact that you’re having trouble with penetrative sex as though it’s an end of the world doom and gloom situation. On the other hand, if you desperately need to have penetrative sex in order to feel fulfilled – and there are plenty of us who do! – and none of what anyone has been suggested above seems correct… Break up now before you get in any deeper.

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