Q: My girlfriend is very interested in me penetrating her using a strap on, which I’ve done in many previous relationships. However, her vaginal opening is very small, and even fingering is difficult. Is there a tiny strap on? I tried to find one with no luck. The itty bitty one I did find would slip right through the o ring of the strap I have. Queer lady gurus, I really hope you can help me/us.

A: Dearest reader, I want to first say thank you. Your concern with your girlfriend’s comfort is more admirable than you probably know. You see, I too have a pretty small vagina compared to others that I’ve experienced, and I’ve had partners make me feel like I’d failed when we realized strap-on sex wouldn’t work out. Your girlfriend is lucky to have a gal pal that cares so thoroughly about her. Bodies are all different, and sex can be weird and have unintentional pressure on it that sometimes makes our bodies behave in ways we didn’t expect. Taking the time to get to know another person’s body so that you can give them what they want isn’t always an easy task.

Even for people with vaginas that can and do accommodate larger toys, the key to getting strapped is building up; but I feel like that’s something you already knew. Start small: use one finger, and then when that feels easy and when she feels ready, add another. Check in often: “Does this feel good? Do you want me to add more? Should we keep going?” Stuff like that. If things are feeling good, add more, and keep checking in. After fingers, move to small toys.

One of my favorite small toys to use with a harness is the Rookie Vibrating Silicone Dildo by Pleasure Works. It’s only about six inches long, and a little over an inch thick. When I warm up with fingers, it’s not much bigger than three of my fingers. I like the Rookie especially for partner play because there’s a vibrating bullet that comes with it, so if that ‘s something you’re into, it can be more fun for the whole party. The Rookie also has a wide enough base to fit into most harnesses—it measures in at 3.25 inches on the longer side, and a pinch less than 3 inches on the shorter side. You can also always buy some O-Stabilizers to make it a little more secure in your harness if it isn’t feeling stable. Use lots and lots of lube, per usual, and listen to what your partner’s words and body language.

Maybe that’s as far as you go the first time, and that’s awesome! Maybe you are able to transition to a bigger toy, and that is also awesome. Also, maybe you try it and realize it won’t work this time. That’s awesome too. If everyone’s in the mood, there are fun things you can do with a strap-on that isn’t penetration. That awkward moment that sometimes happens when you think you’re inside of the vagina but aren’t can actually be hot if it’s intentional. In missionary, it’s super easy to position things so that you can give her a clitoral orgasm if that’s her jam. You can also play with blowjobs, which are my personal favorite thing in the world to give. If it doesn’t work out and you’re both still in the mood to try new things, now’s the time to try them with no judgment. Laugh it off, save it for another time, and find other ways to get busy.

I also want to encourage you to talk to your girl about possibly seeing her OBGYN or midwife for a well-person visit. The reason penetrative sex was difficult when I first experimented with it partially had to do with of the size of my vagina, but it primarily was the result of vaginismus, which is actually pretty common. There’s no agreed upon explanation for why people with vaginas can have vaginismus, but many doctors think it has a lot to do with anxiety around sex. Once I spoke to my midwife about it, she was able to give me a referral to a sex therapist and we worked on a treatment plan together. This may not be the case for your girlfriend, but it’s always good to make sure that everything’s doing what it’s supposed to be doing down there, and a doctor is a perfect way to ensure that.

Lots of things can make strap-on sex difficult. The size of the toy, obviously, but also fear, anxiety, past sexual experiences or trauma. The first time I tried it, I didn’t have a good time. I felt like a failure because I’d built the experience up to be a big and important thing between my partner and I. It didn’t have to be. My partner, who until I’d brought up the idea of using a strap, switched off from the generous and caring lover that she’d been into someone with a one track mind — shoving a silicone dick into my vagina. It doesn’t work that way, at least not comfortably, and definitely not the first time. It’s no wonder I felt shitty; we both had made this into something much bigger than it needed to be. It’s important that you remind your girlfriend that whatever happens, sex is very low pressure. The only goal is for everyone to enjoy themselves. I’ve been made to feel like I let a partner down when strap-on sex didn’t work out, and that’s the last thing you want to do to your girlfriend. Sometimes it just won’t work out, and it’s no one’s fault, so please don’t be disappointed. It’s not the end of the world, and I bet there are still really awesome ways that the two of you can have sex.

Adding a strap-on should just be another fun thing to add to your collective sexual repertoires. The mechanics are really easy. Lots of lube (LOL), go slowly, check in, and start small. You may end up with quite the strap-on collection this way in all sorts of sizes, and that’s really not so bad.

Remember to remind your girl that you are so into her and her body/mind/soul. If the two of you genuinely care about one another—and you writing in and asking for help would imply that there is—means that you’re already at a great starting point. Now get out your lube and get to banging. Bon voyage mon amie!

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