Dear How to Do It,
I have a wonderful boyfriend who is very sexually generous (goes down on me, asks what I like during sex, etc.) but for one thing: He totally avoids me during my period. We don’t touch, kiss, and he doesn’t allow me to go down on him because he says he doesn’t want to be selfish. I’ve asked him what I can do to make him more comfortable and he says he just needs time because he’s always been “grossed out” by the blood and has never engaged in period sex with anyone. Because of the pill, I barely have a flow, and the little there is is still too much for him. For context, we are in our 30s and talking about marriage, and I am a little impatient at thinking of a future with 25 percent of the month off the table for sex. I don’t want to nag him or pressure him, but is there anything I can do to make him more comfortable with some (any!) contact during this time? It makes me feel self-conscious and undesirable.
Dear Seeing Red,
Male discomfort with menstruation is so unfortunate. You’re doing the right thing by respecting his limits, but I think the best course here is to separate sex from snuggles, and focus on the latter while you’re menstruating. Go to your boyfriend and tell him about your feelings. Tell him what you need—kisses? hugs?—and ask him if he can stretch past his comfort zone just a little to meet you halfway. Be open to setting firm boundaries, like “everybody keeps their underwear on,” and adhering to them for the foreseeable future, to allow him to relax during the nonsexual touching that you’re requesting.
You’re right to be wary of diving into marriage without some movement on this front. It’s possible that your boyfriend won’t be willing, or won’t be able, to work through this. Spend some time thinking about how much of a deal breaker it might be if he is never able to penetrate you during your period. Be clear with him about how much of a priority this is for you.
Then again, it’s also possible that your boyfriend may be totally down to tackle this issue. If that’s the case, you can start with the kissing and snuggles, move into being naked together in the shower, and go from there. You can also try turning the lights off. The goal is to step slowly into it to allow your boyfriend time to adjust and acclimate. I hope you can find a way to both honor his limits and to avoid the monthly ban on contact that makes you feel self-conscious and unwanted.
Dear How to Do It,
I’m a middle-aged straight woman. I have never brought a man to orgasm through oral sex. My husband and I have been together for 20 years, and he says he just doesn’t orgasm that way, but I didn’t have success before I met him either. This is something I’d really like to be able to share with him. I do have a pretty strong gag reflex, and my mouth gets tired fast, but everything I’ve read (and seen) online suggests that the hands can make up for this. So … what am I missing? Am I going too slow? Not enough pressure? I know all men are different, but the fact that I’ve never made ANYONE orgasm this way suggests the problem is with me. I’m open to constructive criticism and willing to learn!
Dear Oral Surgery,
At the end of the day, a lot of men just don’t orgasm from oral alone. Or they do but find it needlessly difficult and time-consuming. It has nothing to do with you and doesn’t seem to bother most of them. I’m going to tell you the same thing I’d tell a man in your position: Delivering orgasm does not need to be the goal of sexual contact. It is truly beautiful to see people caring about their partners’ pleasure—prioritizing satisfaction for everyone involved—but you don’t want to get so zeroed in on the orgasmic destination that you miss the journey. Because the journey should be the primary source of enjoyment.
That said, there’s always room for improvement. If your mouth gets tired, learn how to conserve your energy. Run the backs of your nails across your husband’s penis. Open your mouth to breathe hot air on the head of his dick. Brush dry lips across his shaft and glans. Kiss and tickle his testicles. Draw it out and stoke his libido. Keep your focus on the present moment and the immediate pleasure you can provide.
When you’re ready to ramp things up, commit to it. Suck him into your mouth like it’s the thickest milkshake you’ve ever had. Drag your tongue across his frenulum. Use your saliva (or store-bought lubricant) to work the shaft with your hand, jerking up and down and twisting your fist. If he’s open to anal give him at least a tentative press on the prostate through the perineum. Try everything you can think of and see how your husband responds. The Art of the Blow Job is a great XXX video series that can provide inspiration and examples of how to give great head. Porn can never replace sex ed, but I think you’re mature enough to differentiate fantasy from reality.
Remember, you’re just trying to give him as much pleasure as you can—an orgasm isn’t, and shouldn’t be, the measure of your success.
Dear How to Do It,
I’m a 34-year-old, child-free queer woman, and have recently come out of a decadelong relationship with someone who realized they’re asexual, and with whom there had been long periods without sex (understandably). I’ve found that I seem to be hormonally “making up for lost time” and have the sex drive of a teenager, which is both very fun and also distracting. I’ve luckily found someone in my new-to-me small town with whom I have great chemistry and who is equally disinterested in anything serious happening other than seriously awesome and adventurous sex.
My question is, other than being very clear with each other that we don’t want a romantic relationship, how do we ensure those “new relationship” hormones don’t interfere with our plans? So far we’ve been limiting our meetups to once a week to try to keep things casual, but I’m so horny I’d easily be having sex with him multiple times a day, every day. I’m pretty sure I’d “catch feelings” inadvertently if we met more than a few times a week because of the intense hormonal chemistry (we don’t have enough in common for it to be a viable long-term relationship). Maybe a better question is, how do I dial my hormones down a bit? I’ve been masturbating a ton, to no avail. I also am a bit limited by the small dating pool, so I can’t easily find someone else to fill the gaps, so to speak. I’d heard about your 30s being a sexy time, but daaamn.
Dear Second Wind,
Here’s the most emotionally careful way to handle things: Limit texting in between meetups, and be cautious with providing each other emotional support. If the relationship is about the sex, keep it focused on the sex. I know it can be tempting to ask about important life moments and have deeper conversations, especially with someone you’re attracted to, but those behaviors foster attachment. Be careful with the post-sex snuggles as well.
There’s another approach, simultaneously more combustible and more rewarding, which is to foster a friendship alongside your fornication. There’s more risk of catching feelings when you’re physically and intellectually intimate, but there’s also the possibility of developing a rich, mutually respectful relationship alongside your physical rapport. Provided you stay in the present moment and continue to see this person as the whole (incompatible long-term) human that he is, you’ll have an antidote to all the hormones.
As for dialing down your sex drive, cold showers, physical activity, and deep breaths can all help you shift your focus off of your clitoris. Alternately, and counterintuitively, get one of those turbocharged vibrators (the Hitachi?) and wear yourself out—as in orgasm over and over until you literally don’t have another one left in you.
Dear How to Do It,
I’m a bisexual woman married to a straight man. I’ve never had a sexual experience with another woman, but lately I’ve been more and more curious. I wouldn’t cheat on my husband, but recently after some intimate time, I asked him if he would be open to having a threesome with another woman. He said that it wasn’t something that really interested him, but he might be open to it because I was interested. Can I pursue my fantasies under these circumstances? And how does one even go about finding someone to have a threesome with?
—Then There Were Three
Dear Then There Were Three,
I’m so excited for you. You get to explore strange new vulvas. To boldly go where, well, many have gone before. Fortunately, the fact that many, many people have walked the path you’re embarking on means that there’s plenty of guidance available.
There are a few books that delve into ethical nonmonogamy. The authors of More Than Two maintain a blog that covers some basics (along with some completely unrelated subjects). The Ethical Slut is essentially the nonmonogamy bible—which means, yes, you should take it with at least a grain of salt. Whatever you decide to read, think of it as an opportunity to see how other people handle nonmonogamy and learn from others’ mistakes.
Generally, you’ll want to proceed very carefully. Start with conversation. Have a lot of talks about your respective comfort zones. Express concerns and qualms. Work on plans for how you’ll handle it if things go sideways. Fantasize together as a way of getting on the same page. As for how to find someone, there is a whole app for that: Feeld. Alternately you can try it the old-fashioned way and go to parties for people with interesting or complex sexualities and meet people in person. Be upfront about what you’re after and what your boundaries as a couple are, and best of luck finding the right partner to experiment with.