Ask Me Anything: Strapping On For the First Time

June 1, 2011  |  advice

ExperimentallyCurious asked:

What was your first time strapping like? What advice do you have for strap-on virgins? My butch just placed the online order for her first cock, and I have no idea of what to expect.

Go slow. Use lots of lube. LOTS of lube. More than you think you might need, especially at first. It’s just a little messy, which is always better than having not enough. DON’T use silicone lube, as it’ll screw up your silicone toys.

Talk to each other, be as vocal as you can—even “ooh yeah ooh yeah” type of vocalizations will help give cues to each other about what feels good and what is not quite working.

Don’t be afraid to slow each other down or stop. It might just click and work and be amazing, but you also might want to just do it as something to try and to play with, at least for now, so don’t expect one or both of you to get off, especially not at first.

If you’re not used to penetration during sex, you might want to mess around with getting yourself off (or her getting you off, using her hands on your clit I mean) while she’s inside, but without much in-and-out motion, at least for now, while you’re getting used to the feeling of her cock.

The typical porn positions are the best, in my opinion, which is why they are so frequently used—missionary, and doggy style from behind (in various incarnations, like leaning over the bed, or with your head down on the bed instead of on all fours). In missionary, also try it with her sitting up on her knees, with her thighs under your thighs, that is often a really good angle.

Don’t be afraid to touch it, kiss it, lick it, suck it—that stuff can be really hot, though that can also be kind of delicate, so see how your girlfriend feels about it. Sometimes it seems to me, as the strap-on wearer, that I am expected to be the one who does all the action once I put it on, but my point is that you can do things, too. If you aren’t sure if she wants you to touch it (or kiss it or suck on it), ask. “Would you mind if I …” “Wow, I didn’t expect to want to … , but I do, please may I?”

Personally I think just about any sex act is all the more hot with someone saying what they are doing (or want to do), regardless of what it is. Maybe that’s me—I really love language.

Most women can’t come from penetration alone, which I assume the two of you know, but just a reminder that you both might want to start practicing touching your clit while she’s fucking you, either with your hand or, if she can reach comfortably, with hers. It takes some practice to be able to fuck with a cock and use your hand at the same time, but it’s possible! And worth figuring out how.

And from her side … it is possible to get off while strapped on, but that might take some time and practice. For me, I like the harness to be VERY tight, tighter than is all that comfortable around my hips, because I like to be able to feel every stroke against my cunt while I’m fucking. I like the stimulation of a one-strap (g-string style) harness better than a two-strap (jock strap style) harness, but that seems to be the minority opinion, so your milage may vary. She can try adding bullet vibes or butt plugs or the We-Vibe to increase stimulation, though I find those are more distracting than helpful. But if she really likes a vibration on her clit or something in her ass, that might be just the push she needs to be able to fuck and come.

Other than that, in my experience, to be able to come while strapped on, just following the sensation—when you find a spot that feels good, rub up on it, over and over, and see how far that can take you.

Consider anything you do in playing with it an experiment, and collect the data of that experiment. Did it work? Would it work better if one variable was different? Would you try it again? Or was it a complete fail and did not feel good? Gather the data and figure out what you like and don’t like, what was luke-warm and what you might try later if things were a little different.

Did I mention lube?

And … the first part of that question was, what was my first time strapping on like? Well, to be honest, my first time strapping on was to peg a guy, my boyfriend of about 5 years that I was with in high school. I bought a strap-on when we broke up, and I came out as a lesbian, and it was a tiny silicone thing that was very hard silicone and black and narrow. I do still have it, actually, I keep thinking it might be a good size for anal sex, but then again, now that I have the Spur why would I use a cock that was so hard?

We then went cock shopping together and bought a cock that was roughly the size and shape of his, which was what I pegged him with. It was fun enough to peg him, but it also made me realize that I was (really really for sure) a dyke and wasn’t that into it.

I did fuck my first girlfriend with a strap-on, but we were more of the I-do-you-you-do-me type of couple, so we took turns. It took quite a few more years before I felt like I had a cock that was mine—really not until I ended the relationship with my college girlfriend and started dating femmes exclusively. Which I have widely chronicled here!

It’s been a long journey to claiming my cock-centricity and cock confidence. Actually, I teach workshops on Cock Confidence now, in case you’d like to attend one—I’ll be doing it next at Good Vibrations in San Francisco in August.

Anything else y’all would recommend? Any other tips for first-time strap-on users?

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5 Comments


  1. Hi there – longtime reader, first time commenter. My advice for first time strapping is: Let it be possibly awkward, let the experience be whatever it is, and let it be an opportunity for you and your sweetie to be closer.

    It’s been a long time since I started playing with strap-ons, and I don’t recall my first time wearing one, but I do remember feeling some performance anxiety. Actually, that feeling has never entirely disappeared, though it has minimized, and it’s allowed me to better appreciate the times when I’m not the one wearing the cock.

  2. The first time I had strap on sex(receiver), communication was key. Unfortunately we bought a cheap harness and the o ring had a slight gap in it. The open space in the ring kept “grabbing” at my lady bits and about an hour later there was swelling. Not good at all.

    Now with a year of experience and a slightly more spend-y harness my partner and I are having some pretty delicious sexy times with our harness and cocks:)

  3. thank you for this beautiful words. – a femme

  4. I think that the harness is extremely important. I used a cheap harness at first but never really felt in control. Then I bought a SpareParts harness and finally realized how satisfying the experience could be! You get what you pay for, I suppose.

  5. I was so awkward and embarrassed the first time I wore a strap on. I used to have to hide under the covers to get it on or have all the lights off – anything so that she didn’t see me having to strap-on my cock! It was humiliating to me that I didn’t have a real cock and I didn’t want her to see the process of me putting it on instead of whipping it out of my pants.

    After a few months, all my shy ebbed away but I think its something to keep in mind: wearing a cock for the first time can be really vulnerable especially if the wearer is butch because it is so much more than just a piece of silicone. It really does become her cock. My partner was always so good at seeing that and respecting the cock as an extension of my masculinity – my self – and not just some toy we ordered from Babeland. Because of she really saw me and saw what that cock meant to me, I was able to truly embody it and own it for myself. Now we just fuck like crazy with it and I freaking love it!

    Oh, and I totally agree with L.A. : forget cheap harnesses. I love my Aslan leather harness. So worth the money.

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