The Frisky Feminist

From the Archives: Strapping It On In Style

[NSFW images after the cut] Q: I could really use some help picking out a good harness. I know you’ve mentioned strap-on play and my husband is interested, but we tried it once and I HATED it because I couldn’t figure out the angle or rhythm and the harness kept slipping. I’d like to give it a fair shake with good equipment. Many pervy thanks!

A: A good harness can definitely make a difference–but full disclosure here, the first four times (at least) that we tried pegging, it was awkward and tricky and a little frustrating. Pegging (which is slang for a woman fucking a man in the ass with a strap-on) often takes a bit of practice; if you’ve never worn a strap-on and done the penetrating, the logistics are pretty different than what you might be used to when you’re the one receiving penetration. So, first we’ll talk about the different kinds of harnesses you have to choose from, and we’ll also offer some suggestions based on our experience for helping things go more smoothly.

Two-strap style harness. Image from

There are two main harness styles ““ G-string and two-strap. G-string harnesses have one strap that runs between your legs from front to back, and two-strap harnesses have two straps that go around your thighs. There are also harnesses that look more like underwear or shorts, which some people prefer because they find them more comfortable or because they come in some cute, sexy styles. From our experience and from what we’ve read on various sex toy sites, two-strap harnesses tend to offer a little more stability and a tighter fit, though many people enjoy the extra friction that comes from the G-string style (we found it to be a bit too much friction, but to each their own). Harnesses usually fasten with either buckles or D-rings, and there are advantages and disadvantages to both ““ buckles will fasten very firmly, while D-rings offer a lot of room to adjust but can slip a little, especially as the harness gets older.

G-string style harness. Image from

How the dildo fastens in the harness may be related to some of the difficulty you’re having as well. Most harnesses have an O-ring that you stick the dildo through, and it’s important that the ring be the right size for the dildo–too big and it might flop around, too small and the dildo might start breaking at the base. The right size O-ring should hold the dildo snugly and keep it in place, and harnesses (either the box or the product description) will usually specify if you can swap out different sizes of O-rings and thus different sizes/styles of dildos. There is also the Vac-u-Lock style strap-on–instead of an O-ring you stick the dildo through, a small plug snaps into the harness and dildos made specifically for this style slide onto the plug.

For even more information about harnesses and the pros and cons of the various styles, check out Babeland’s guide and Blowfish’s article; both are full of tips on how to find a good harness and the range of options and styles that are available. (Also, on the original post, Persephoneer whatimages suggested having a look at Midori’s instructions for making a harness from scarves; while we haven’t tried this yet, we say it’s definitely worth a shot!)

A harness that isn’t slipping and sliding around will go a long way toward improving your experience, but here are a few other things that we found helpful when we first started exploring it:

  • Explore his ass. When we first started out we had a lot of trouble achieving penetration with the dildo popping out. Paperispatient says: I realized that part of the problem was that I didn’t have any idea what direction/angle I needed–I had no idea how the rectum curved or what direction it angled in the body. I took awhile and just fingered him so that I got a better feel, literally, for what I was trying to penetrate.
  • On a related note, try holding the dildo in your hand and penetrating him with it. It can be difficult to navigate an internal body part with an object that doesn’t let you feel what’s going on, and holding it in your hand gives you more control and can really help you see what angles facilitate penetration best and what feels the best for him.
  • Make sure he’s really turned on and relaxed before you try penetrating him with the dildo in the harness. The other part of our problems stemmed from us being overeager to get to the good stuff and skipping past some very necessary foreplay and preparation. Stick with fingering until his muscles feel relaxed and you can move your fingers easily and everything feels good for him. Internal muscles squeezing the dildo can definitely interfere with your ease of movement, plus it will feel the best for him if he’s completely ready.
  • Try lots of different positions and different kinds of movement. You may need to hold onto the dildo at first until you figure out what works for you–paperispatient was under the impression that she’d be able to start just humping away, but guiding the dildo inside and holding onto it at the beginning helped with the popping-out problem we were having. Just as you probably experiment with different kinds of motions and thrusts when you’re on top during PIV sex, try lots of different movements with your hips. You might find that moving your whole body instead of just your hips helps you keep the rhythm. Have him move around too; him on his back with his hips tilted up and legs spread wide might work well, as might him bent over the bed or on his hands and knees. Like we mentioned before, exploring these positions while using the dildo with your hand first might be really helpful for figuring out the right angle.
  • Future Mr. paperispatient says: Although you should definitely stop if there’s significant pain or discomfort, it might take a little while before it really starts feeling good for your husband, so he’ll need to be patient as well. We’ve both been on the receiving end of anal sex more than a few times, but it still usually starts out just feeling kind of weird, with the receiving partner thinking something along the lines of, “Huh. Maybe this doesn’t feel quite as good as I remember it feeOH WAIT YES IT DOES MORE PLEASE.” That’s our experience, at least.

It’s easy to get discouraged, but trying to stay patient and putting in lots of practice (darn, huh?) should really help pegging be more fun for both of you.


Keep the great ques­tions com­ing! (Hee.) Got a ques­tion to ask, sub­ject you’d like us to dis­cuss, or myth you’d like us to bust? You can e-mail us at or send us an anony­mous mes­sage via the spiffy, new Ask Us! fea­ture here.

By paperispatient

I recently earned my MA in women’s studies. I enjoy reading, working out, playing Scrabble, watching cheesy movies, and cooking yummy vegetarian meals with my partner and Frisky Feminist co-author, Future Mr. paperispatient.

One reply on “From the Archives: Strapping It On In Style”

Nice article!

A little late to the party here but I have a couple of things to add…

Erections or lack thereof – Your man may have no erection, a raging erection or his erection may come and go while you are either stimulating him with fingers, toys, or your actual strap-on. ALL these are normal, so do not look for an erection as evidence he is enjoying himself. If you want to know whether or not he is enjoying the experience – just ask!

For easier penetration – tell your man to push out with his muscles just like he is trying to have a bowel movement at the moments of penetration. This will allow the sphincter muscles to open. Anal sphincters will open automatically when there is something inside that needs to come out, but not when there is something outside that wants to come in.

Ruby Ryder


Leave a Reply