What To Do If You Can Orgasm Alone, But Not With Your Partner

Illustrated By Anna Sudit.
You've written me with questions, and this week, I'm answering some. Check Refinery29's Snapchat Discover Channel every Saturday for answers to more of your love and sex quandaries.
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"I've been having a little trouble with finding a balance between respecting myself and being a sexual being. What I mean by that is, I like sex...a lot. I've been with a couple of guys, and I've recently started to have a casual relationship with someone I've been intimate with before. Sometimes, I feel bad, because it feels as if I should be saving myself for the 'man who will love me forever' and not using my body in situations like this. How do I deal with these conflicting thoughts and accept the side of me that, well, loves sex?"
Liking sex needn't say anything about you other than that you like sex. It can be so hard to disentangle our parents/peers/pastors/priests/politicians’ hopes for our sex lives from our own (and doing so doesn’t necessarily mean that these hopes are different), but if we are going to claim our lives as our own, it's work we have to do. In your question, you present "respecting yourself" and "being a sexual being" as opposites — but respecting yourself includes accepting and celebrating your sexuality, and at this moment in your life, that just so happens to include casual sex. It’s true that good sex isn't worth feeling unsafe or shitty about yourself. But if the people you're with are treating you with decency, neither is it worth it to berate yourself for enjoying something that humans (not just the male ones!) have evolved to enjoy. I say to enjoy without apology or shame.
"What's the best way to prepare yourself for anal intercourse?"
While your clothes are still on, talk with your partner about your and your partner's past experiences with anal play. What did you like? What didn't you? Then, whether or not you've had anal before, discuss how you'd like it to go this time and any concerns you have. This conversation has the added benefit of building anticipation before the act (sexy). When you're ready, apply lube — water-based if you're using a silicone dildo — with reckless abandon. When you have enough lube on both the penetrating penis/dildo and the receiving anus (which, reminder, does not self-lubricate), add more. Now you have enough. The receiver should relax his or her muscles, and the penetrator can start with fingers, adding more as the receiver adjusts, and building up to penetration with a penis or dildo (there are also graduated butt-plug sets you can try). Don't rush. Remember that anal doesn't exempt you from condom use if there is any risk of STI transmission. And, the receiver should set the pace — he or she is in charge here. And have fun!
Illustrated By Anna Sudit.
"I've been with the same guy for going on three years, and my chronic inability to orgasm during sex is sort of becoming problematic. When I'm masturbating? I have no problem. But my guy is starting to get insecure that he's bad at sex, which, whatever, I've reassured him billions of times that it's just different for women. I've had maybe five male partners in my 23 years and have never reached orgasm with any of them. I'd love to have the full gamut of the experience and know what orgasming with someone feels like."
I’ve had the inverse experience with a male partner who didn’t orgasm from sex with me — not never, but not often — although he came consistently on his own. I believed him when he assured me how much he enjoyed our sex, but I couldn't help but feel that on some level, I was failing as a partner.

But guess what I had to do? I had to take him at his word, get the fuck over it, and enjoy myself, too. Often, the partners of people with anorgasmia — whether primary (they never orgasm), secondary (they used to, but don't anymore), or situational (they don't orgasm in certain contexts, for example during partnered sex) — allow their own insecurities to eclipse their partners' issues. I don't want to say "problem," because not everyone sees not orgasming as such. At the same time, yes, it would be nice to come with your guy. While orgasm isn't the be-all-end-all of sex, it is, as you said, part of the full gamut of sexual experience — and it's a really, really fun part.

A question for you: What are you counting as "sex" here? It's estimated that only 25% of women orgasm consistently from vaginal intercourse, mostly because vaginal intercourse doesn't offer much in the way of clitoral stimulation. Bumper stickers teach us that in religious pluralism, there are many paths and one mountain. My addendum is that there are many ways to reach orgasm, and no one way is "right." An orgasm is an orgasm, and you might need manual or oral stimulation or maybe a toy to have one with your partner. (I will advocate for vibrating penis rings until I draw my dying breath. My last utterances to my great-great-grandchildren shall be songs of their praises. I will also never forget an interview I once did with a woman who had never had an orgasm until, at age 26, she went home with a casual acquaintance who used a come-hither fingering move to stimulate her G-spot just so. She came four times. This woman gives me hope.) Think about how you get yourself off, and consider demonstrating your masturbation techniques to your partner for him to try on you.

Technical suggestions aside, it's possible that your form of anorgasmia stems from emotional rather than physical causes. If further exploration with your partner isn't getting you where you want to go, I'd recommend reaching out to a local sex therapist for a consultation. A good therapist can help you identify the patterns behind your inability to reach this particular mountaintop.
The Bed Post is a series that explores what holds us back from sex and love with whom we want, when we want, where we want, and how we want — because we all deserve sex and love lives that are not only free of evils, but full of what is good. Follow me on Twitter at @hlmacmillen or email me at hayley.macmillen@refinery29 — I’d love to hear from you. Find all of The Bed Post right here.
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