Ask Professor Foxy: How Do I Get Past His Not Cumming?

This weekly Saturday column “Ask Professor Foxy” will regularly contain sexually explicit material. This material is likely not safe for work viewing. The title of the column will include the major topic of the post, so please read the topic when deciding whether or not to read the entire column.
Dear Professor Foxy,
I’m sure you get this all the time, but I feel like my issue may be the first you’ve heard. My boyfriend and I recently had sex (both of our first times), and have had sex a handful of times since, and he has never cum. He thinks it’s because he had a back problem a couple years back, which made one of his legs almost completely numb, along with parts of his torso (including, apparently, an important area). Before we had sex, we’d fool around, with me touching him, and I could never get him off, which embarrassed me and made me feel like it was my fault because I’m not all that experienced. He masturbates, so I know it is physically possible for him to cum, though. I just can’t figure out how to do it–and I think that for me to make him cum, it’s going to involve going outside of my comfort zone (I’m not down with oral sex quite yet).
I know it’s probably just a physical thing, not just me, but I’ve been feeling guilty about it because I have these AMAZING orgasms every time.
We’ve been trying different things for a month or so and can’t seem to get past this pretty major block. I know it’s frustrating for him, even though he tries not to show it, and it’s possibly more frustrating for me, because I feel like I’m getting nowhere. He doesn’t give me a lot of feedback either, I wish he’d give me some heavy breathing or a moan or something to let me know I did something right.
We’ve talked about it a lot and where we are right now is agreeing to keep trying things, trying not to put pressure on cumming, just enjoying the experience. But how can I hurry this along?
Thank you,
Frustrated and Confused
Dear Frustrated,
Your last paragraph sums up your issue: you want to be supportive and you want him to cum. In this case they are two, possibly conflicting issues. I understand the desire to hurry this along, but in order to truly just enjoy the experience; you need to work on actually letting go of the desire to hurry it along. The pressure to cum is the natural enemy of orgasm.
What you need are steps and feedback. You are not getting a physical or the vocal response and it is hard to feel like you are a good lover without either of those. Have you asked him for vocal feedback? Can you tune into other parts of his body? Do his arms tighten when he aroused? His toes? If he is not comfortable making noise, can he hold on to you and tighten when he is aroused? It is hard for you to work in a vacuum., but men are often taught that men should not make noise during sex.
You don’t need to go out of your comfort zone, but you should actually see what makes him cum. Has he jerked off in front of you yet? It may also be about him relaxing with another person. How has his back problem impacted his self-image? He needs to not feel pressured and you should not feel guilty about your orgasms, these things won’t help either of you.
I would also go one step further and take him having an orgasm off the table all together. Don’t make it the goal (explicit or implicit), instead focus on fun and exploring what feels good on his body, what turns him on, and getting to a place where orgasm feels much less important. By doing this you are creating a space where orgasm can happen and is not the goal, but just another activity.
Best,
Professor Foxy
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