I'm coming, I'm coming, I'm......not.
Basically, my problem is that I cannot seem to cum during oral sex or intercourse. If she uses her hand then I reach orgasm within an acceptable space of time. However, when having sex or receiving oral sex, the feelings build up but never quite reach the point of orgasm. Is this normal? Is there anything I can do?
When it comes to sex and particularly to the issue of orgasm, expectation can be your worst enemy. As soon as you are worrying about whether you are normal or stressing about a specific event happening or not happening then you’re creating anxiety for yourself, which is a huge barrier to actually enjoying yourself!
Focusing on orgasm (and the details of how you’re getting there or not getting there) is what I’d call “goal-oriented” sexual activity. When you’re being goal-oriented in sex you are just focusing on the end event: the orgasm. While being goal-oriented in life is not always a bad thing, for sex it can be a little troublesome. Another way to look at sex is from a “pleasure-oriented” perspective. What I mean by that is focusing on the moment and the sensations, not worrying yourself about what will happen next.
I know it might be easier said than done, but try throwing away your expectations of what is “supposed” to happen and what timeframe is “acceptable”. The truth is that there is no script for exactly how any given sexual encounter is supposed to unfold, and there is no such thing as an acceptable amount of time, empirically speaking. How are you defining “acceptable space of time” for yourself? I think that might be a good place to start thinking; you may find that you’re putting stress onto yourself to live up to some expectation that is not a reality for you, or something that you’ve heard that’s “normal” that may not actually be based on any kind of real information.
Your question mostly asks about sex with your partner, but I’m wondering how the orgasms for you go when you’re by yourself? Have you ever masturbated? Do you orgasm regularly when you masturbate? If you are able to have orgasms on your own, or even if you’ve ever had a wet dream, them I’m guessing that you are physiologically functioning fine, which means that the issue you’re describing with your partner has more to do with your headspace than anything else. That’s pretty common—people hold a lot of anxiety about sex. Anxiety is not a friend when it comes to pleasure and fully being in the moment sexually.
An orgasm, by nature, involves letting go and being vulnerable to pleasure, your own body, and whomever else might be involved in the scenario that’s potentially leading to orgasm. Many of us have received negative messages about our bodies or about sexuality, and sometimes that can interfere with our ability to let go. Also, we might just not feel totally comfortable with a partner or in a specific situation, which will make having an orgasm pretty difficult. For some guys, handjobs may feel safer—it’s more like masturbation and thus a feeling that may be more familiar for some guys—and oral sex or intercourse is just a new territory, something that feels scarier or makes you be a little more vulnerable than you’re used to. Just like all women do not orgasm from penile-vaginal intercourse alone (most won’t, in fact) not all guys are wired the same. Essentially, there’s nothing inherently wrong with you if you don’t get as much pleasure from one activity as you do from another. It’s all personal preference and personal experience, and it’s ok.
But I have a couple of suggestions about how you could approach this issue since you’re expressing worry about it. My first thought is this: don’t make this an issue. Try to keep a pleasure-oriented view of sex and avoid the goal-oriented thoughts. The more you worry about your orgasm and when it’s going to make its grand appearance, the less likely it will be to happen. Instead, focus on whatever feels good sexually. Receive pleasure, and by all means make sure your partner is also feeling good!
The importance that good communication plays in fostering positive sexual encounters simply cannot be overstated. If your partner is pressuring you about your lack of orgasm (you didn’t mention one way or another how she feels about the situation, so I’m wondering if you’re putting the pressure on yourself) then let her know that her pressure isn’t something that is helpful, nor is it going to help you orgasm. We are much more likely to feel better about ourselves, feels sexy, feel wanted, feel attractive, feel all around awesome when we are having sex with a partner with whom we feel connected and able to communicate.
If you know what feels good for you and what helps you to orgasm, tell her. Better yet, show her! If you’re not sure what feels good for you then I’d recommend taking some time for self-exploration so you can have a better idea of what you like. Masturbating for someone can be not only really hot, but a totally educational experience. Your partner can see what you like, learn some tricks about what you’re into, and also gets to see you really enjoying yourself. Maybe your partner would also like to show you what she likes on herself (which isn’t part of your question but I’m all about reciprocity and making sure everyone in the encounter is getting to enjoy themselves and not get bogged down in performance anxiety). Mutual masturbation (masturbating together) or watching a partner masturbate also has the bonus of being a sexual activity that is incredibly low risk for STIs as long as no fluids are exchanged.
When you take away orgasm as the central focus of sexual activity (replace it with pleasure, remember?) you have more opportunity to just enjoy yourself. Talk about what you like with your partner. Find out what she likes. Do those things! Take joy from both receiving pleasure from her and also from making her feel good. Once the communication lines are open some more and you’ve taken some pressure off of yourself then the orgasms will come more freely, or from other activities. And, if not, enjoy the handjob; there’s no shame there, and that orgasm is no less valid, pleasurable, or rockin’ than an orgasm achieved through other means.
Here’s some more food for thought: