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Dear Kiki: I want to go ‘there’ with my partner. How do I ask?


Questions about love and sex in the Iowa City/Cedar Rapids area can be sent to dearkiki@littlevillagemag.com (queries can also be sent anonymously using this form). Questions may be edited for clarity and length, and may appear either in print or online.

Illustration by Jav Ducker

Dear Kiki,

I’ll get right to the point. How do I ask my partner that I want a finger (maybe even fingers) in the bum? We’ve been together for nearly three years and there’s a lot of love and trust between us, but I just can’t find the words to ask.

Dear On Point,

Ah, that age-old dilemma! There are probably as many different answers to this question as there are people out there wondering it right now.

First and foremost, no matter your or your partner’s experience level, remember to always be cognizant of good hygiene: yours and theirs. Give them all the reassurances they need that you’re keeping it clean back there, but also make certain that whatever digit they’re using has the nail trimmed close and the cuticles smooth. Be sure, too, that there are no cuts or scabs or sores. It should be as blemish-free as any other appendage you put into any other of your holes—more so, because the risk of infection is greater.

Now, for the neophyte: You say “(maybe even fingers)” as though, perhaps, you’re not even sure yourself what you want. Which is fine! But exploring new things with a partner is a decidedly different vibe than confidently asking for something you know you’ll enjoy. If this is the case, you need to search your heart and determine exactly why you’re asking first. Because your partner will ask (or, if they are as reticent as you, write to me later about) whether you want to explore because you are bored.

Whenever someone wants to branch out sexually in an established relationship, pride and self-worth come barreling into play. Is what your partner currently does no longer fulfilling you? Are you looking to “spice things up” because you’re no longer turned on by them? It shouldn’t matter what your answers to these questions are — what matters is that you know the answers for yourself ahead of time and that you are 100 percent honest with your partner about them.

If what you’re looking for is a relationship kickstart, you should frame your question that way — and you should be aware of and open to the fact that your partner might have some suggestions and requests of their own. It’s perfectly healthy to need that after several years together. But it’s also perfectly healthy for your partner to feel shaken by the admission and need some extra reassurance.

One fun way to broach these topics if you’re exploring together is to find some (feminist or otherwise progressive and non-exploitative) porn to watch together. If you do your research first, you can find one that involves what you’re hoping to try, and when it happens on screen, note that it looks fun and you’d like to try it.

If you have, in fact, walked this road before (on your own or with other partners), know you like it and simply want to insert it (*cough cough*) into this current relationship, the conversation is different. You don’t need to maneuver as many feelings, perhaps — but you do have to do as much soul searching: in this case, less exploring why you want it and more exploring why you’re hesitant to ask. Do you think your partner will judge you morally? Are you concerned their reaction will be more one of scatalogical disgust?

If it’s the former, just take a deep breath and forge ahead. This is a bandage you need to rip off! If you suspect your partner is in moral opposition to something you find normal and pleasurable, that’s an unpleasant but necessary conversation to have at this point in your relationship, because it may reveal deeper disconnects.

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If it’s the latter, you may want to consider alternatives, at least when getting them used to the idea. Would you be open to objects other than their fingers in there? A trip to your local (or online) sex toy store would be a fun, low-key way to kickstart that conversation. Just because they may have hang ups about it doesn’t mean they don’t want to please you, and finding a middle ground should be fun.

xoxo, Kiki


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