Hi Ruth:

Most of what I know about this is from my own experience and from asking my buddies, and there’s not much real research out there to read on this — so here’s my thoughts on this from what I know of strap-on technology and what I know of anatomy and what I have experienced.

First, a word of caution. I think a lot of folks aim to be able to do this — to get off while strapped on in this way — because we think we should be able to do it, because we read it in smut stories (which I myself am guilty of penning), and because we’ve fetishized the kind of masculine/feminine friction that comes with fucking in this way. But the truth is, our bodies aren’t really built to receive stimulation like that, and it’s very possible that this kind of stimulation on your clit and cunt just won’t be enough or in the right spot or precise or hard or fast enough to get you off. You might need something else — fingers on your clit, a vibrator underneath, or some other sort of stimulation.

I want to challenge, just a little, the want to do this in the first place. Sometimes we — butches, trans guys, masculine of center folks in general — fetishize these masculine ways of fucking and it’s actually to our detriment, because we end up being more frustrated and less satisfied during sexual play. We end up getting off less, because we are aiming for this one particular way to get off. So just give it a little bit of thought: Why do you want to be able to do this? Is it because you fetishize your own masculinity and the friction between you and your femme partner? Is it because you think it’s the only way you should be getting off? Is it because of the dysphoria of having your body touched the way that is stimulating feels feminizing? Is it because of some internalized homophobia which says that getting off this way is the “real way” to have sex? Is it because you have deconstructed and dismantled gender and sex so much that you’ve come back around to fetishizing the very things you’ve deconstructed?

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Double-strap Adjustable Harness
We-Vibe 3
Clit Pump]It might be none of those things — and in general, the why isn’t the most important thing, but I think it’s worth questioning, just a little. I’ve seen folks get into unsatisfying places in their sex lives for the wrong reasons, and I want to discourage that if possible. I think the most important thing is feeling and being satisfied. I’m pretty similar to you in presentation and gender, being mostly stone most of the time (meaning, primarily, that I am in charge of when and where and how I receive touch) and focusing on my femme bottom partner’s pleasure more than my own, and I know that sometimes I get caught up in my cockcentricity and stone top-ness, and then I start getting really wound up, and realize two weeks later that, even though she and I have been fucking, I haven’t been coming, and I’m unsatisfied and frustrated. And if I can remind myself that it’s not the only way to come, and actually use my hand once in a while, I tend to be a bit more satisfied.

But that’s just me — maybe you won’t fall into that rut. And now that the word of caution is out of the way: I completely understand why you’d want to do it. I love getting off this way. Love it. I fetishize it, big time. I spend so many hours a day talking and thinking and writing about gender and sexuality, pulling each thread of heteronormativity out of my head and untangling it from my own thoughts about what’s really true in the world, that I end up fetishizing this kind of masculine/feminine friction.

I can get off while strapped on and fucking, but it’s not frequent. I can’t quite seem to control the variables enough to do it on command or even just if I try really hard. I’ve never been able to come from a blow job or hand job. I think the stimulation just isn’t quite enough for me.

It all depends on how you come, really. Some people are incredibly sensitive and can get off by someone just touching them lightly on the outside of their clothing, and some others (like me) take at least a good ten minutes of direct, precise, careful stimulation before being even close to getting off. (Unless, you know, I’m extra turned on before the touching starts — more on that later.) I get overstimulated easily, so sometimes the smallest thing can take me from oh right there to oh god stop ow. I know I pretty much have to have direct stimulation on my clit, so I’ve had to figure out how to get that while strapped on and fucking. Maybe you need a whole lot of pressure, or a lot of vibration, or something on your G-spot. Bring those things to mind and start playing with the strap-on technology to see what can get you there.

Here’s some tips that have worked for me:

1. One strap harness: This has been essential. It wasn’t until I had a one-strap that I ever got off while strapped on, because of the way the single strap hits my clit. My current favorite is the Aslan Jaguar G. Some folks, though, have said that the two-strap harness is essential to their getting off, precisely for the same reason — because of the way it hits their clit. I think this depends on how you like to wear your harness, how it fits your hips, how tight you like it, and where the straps and base of the dick hits. Experiment! Try it extra-tight one time and more loose another. Try it high on the hips or low on the hips. I highly recommend the Aslan Leather Pleasure harness if you aren’t sure you prefer a one- or a two-strap harness, because one of the straps is removable and can be switched back and forth into either.

2. Keep it Tight: If I notice I’m close but not actually coming, sometimes I tighten my harness up and that does it. I need it tight, I mean tight, in order for it to work for me.

3. Fluff: Sometimes I’ll get myself worked up before I strap on. Usually I use my hands, and I’ll stimulate myself to the point that I’m just about to come, then stop and pause for a few minutes, then repeat. Often I do this three times, and usually the third time doesn’t take long at all for me to feel like I’m about to come, and that’s when I’ll go back into the bedroom and strap on.

4. Outside Stimulation: I know that when I watch a few videos in particular, or read certain stories, it’s easier for me to get off in my own masturbation practices, so that applies to getting off while strapped on as well. Watch some porn or tell some stories with your partner. Get yourself worked up in whatever way you need to before the strapped-on part even happens.

4. Lube: I come much easier if my clit is slick and wet. Sometimes I actually reach under my harness straps to add lube to my bits — it helps.

5. Dirty Talk: I mean this is just good in general, but sometimes my girl really gets it going and that will push me over the edge. Particularly if I’m strapped on and fucking her, and she starts talking about how she wants me to come inside her — I love that, and it can, sometimes, do it for me.

6. The We-Vibe: This is a kind of ingenious little vibrator with lots of speeds that you can wear underneath a harness. One side of it slips inside (or right on the outside of your hole, if you can keep it in place) and one goes over your clit. You can wear it under a harness easily and some harnesses even double as a great strap for keeping it on. If you like vibration, this might be worth trying. I know it’s kind of “cheating” — that you said you don’t want any other sort of stimulation — but if the option is to wear this or not get off, it’s probably worth it to wear this, right?

7. Pumping: Clit pumping can make your clit more sensitive, and bigger, which can make it easier to stimulate. It can also make you a little less sensitive, so I wouldn’t try this unless you are pretty sure you are not so sensitive. Try it on your own for about ten minutes a day for a week, or try it just before you’re going to strap on.

Experiment with the things in here that strike you as interesting, and collect the data. And remember: your bits aren’t exactly built for this. You might be one of the lucky, sensitive guys who can come easily through not much stimulation, but you might not be. There are lots of ways to get off, and all of those are just as legitimate as this one.