Agony Aunt

Dear How to Do It,



I’m a straight woman who has a reoccurring problem with new sex partners. I insist on condoms for penetrative sex unless a relationship becomes exclusive, but I’ll engage in oral and light non-penetrative genital-to-genital contact without them. I’m well-aware those activities are not risk-free, but that’s my comfort zone. My partners are generally on board with wrapping it up at the beginning of the act, but sometimes they’ll take the condom off midway through because it diminishes their sensitivity. No one has ever slipped his penis back in pretending it’s still wrapped. The good eggs have accepted stopping for the moment, or engaged in petting or oral instead. But too often my partner has agreed not to enter me unwrapped, but will then rub his penis against me in a way that feels great and is essentially like knocking at the door begging to be let in. I’ve sometimes relented against my better judgment because I’m overcome by desire and I don’t love the feel of condoms either. One guy suggested we just do hand stuff instead, but then once I was really lost in the moment, he slipped his penis in without a word. I went stiff, and stopped it immediately, and never saw him again.


The culminated effect of these encounters has been to drastically damper my pleasure once the condom comes off. I feel hyper-vigilant about protecting my reasonable boundary, preventing me from letting go. I also feel resentful that it falls to me alone to keep the safe sex practice we originally agreed on, guilty and ashamed that I’m not getting him (and often myself) off, and sexually frustrated because I prefer condom-free sex too and it’s literally being dangled onto me. How do I reinforce this boundary without killing the mood with accusatory forewarnings or by creating an air barrier between our bodies? Or should I just jump out of bed and into a cold shower once the condom comes off? Also, can you suggest the most pleasurable condom brand (preferably one that doesn’t leave a poison taste on genitals)?


Dear Unwrapping,

I am so very sorry you’re dealing with this. I’m especially sorry that man put his ungloved penis back inside you. There’s been debate about whether that counts as sexual assault or should be illegal in a slightly different way, but it is never OK to penetrate someone without protection against their wishes. It’s also never OK to penetrate someone with protection against their wishes, just in case anyone is wondering. Frankly, I’m not thrilled with the begging types either.

For my part, I like to catch my partner’s penis between my upper and lower leg (nestled behind my knee) if it gets too close to my genitals during a romp before the condom goes on or after it comes off. It’s a bit cheeky, but does tend to keep them from risking fluid exchange. Hands work too, as do elbows, mouths, or just kicking the dude out of bed and telling him to come back when he can approach you with respect for your boundaries. I’m not sure how you can reinforce a boundary that is being ignored without killing the mood. I do think some moods are worth killing.

I can’t suggest the most pleasurable condom brand because I’m not you, so I’m not sure what works for your body. I’m sensitive to latex, so I tend to use SKYN (disclosure, I’ve worked with the company in an advertising capacity) or other non-latex but still FDA-approved condoms if the guy has a problem with my preference. Flavored condoms are a gagfest for me, but you might prefer them to the normal taste. Get some sampler packs and try some new ones out.


I just...have my rape sirens blaring. You can't change the agreements of consent. This advice seems utterly horrendous.