How to Do It

My Boyfriend’s Absurd Anatomical “Gift” Is Causing a Little Problem in the Bedroom

A woman in front of a blinking eggplant.
Photo illustration by Slate. Photo by Favor_of_God/iStock/Getty Images Plus.

How to Do It is Slate’s sex advice column. Have a question? Send it to Stoya and Rich here. It’s anonymous!

Dear How to Do It,

I’ve been with my guy for two years. While we have fantastic sex, one thing I love is missing: anal. I’ve enjoyed anal sex in the past and want it with him, but he has an extraordinarily long, fat penis. It’s something to behold. And Tab A just won’t fit into Slot B. To get used to his size, I’ve tried graduated training plugs but the largest is still smaller than his “plug.” It’s worth noting that his length is not preventing penetration—his girth is.

So, I’m literally asking “how to do it,” anally. Thanks for your, um, input.

—Not Just the Tip

Dear Not Just the Tip,

Inflatable butt plugs. I’ve seen them starting at three inches in diameter before pumping and expansion. You may also be able to find thicker, uninflatable plugs. Try your local sex shop—they may be able to special order you something, too.

If fingers feel OK for you, there’s always the duck bill stage of fisting. I’ll explain: To fist, you go through a number of stages. At one point you have all four of your fingertips squished together with your fingers fairly flat and your thumb tucked in, and the hand looks like a duck’s bill.  On my hand, that’s eight and a half inches circumference. On his, I image that’s more. It might help dive into the fun and fabulous world of fisting—just use plenty of lube.

The same goes for the anal you crave: Take it slow and gradual, and keep things well lubed. Try breathing exercises to help you relax. There’s one I use where I breathe in for four seconds, hold my breath for seven, and exhale for eight. I do these four times, 76 seconds total. On the inhale, feel your breath going all the way through your chest, into your gut, and down into your pelvic floor. If you can do a Kegel clench during the breath hold, do that. You can try other breathing techniques as well—really anything that encourages you to focus on your body and brings your awareness to relaxing the parts you’d like.

Dear How to Do It,

I’m a woman with a voice kink. It usually doesn’t play a huge role in my sex or dating life, but when someone does have a really nice voice, I find it incredibly attractive. I recently entered into a sexual relationship with one of my friends who I had always thought had a lovely voice. I’m incredibly attracted to him—like, I can orgasm JUST from him touching my arm during sex—and that coupled with my voice kink has led to an interesting new sensitivity: His singing/humming voice makes me orgasm. Normally this would just be a fun little nugget of information that doesn’t really affect any major part of our lives, but my friend is a member of our college chorus (and just a general idle hummer/singer of songs) and I would like to be able to see him perform. How do I stop myself from being so sensitive to his voice/him?

—Audiophile

Dear Audiophile,

Have you attended a chorus performance and experienced inappropriate arousal? See, I’m wondering if being in a public setting might prevent orgasm, and it’d be simple for you to experiment.

Another thing you can experiment with is exposure. Sometimes new kinks or quirks have a unique sort of power that stems from novelty. We aren’t used to them yet, so we’re hypersensitive and reactive. If you get enough of this stimulation, it might lose some impact.

Otherwise, you might have to get creative with earplugs and settle for watching—but not hearing—the performance.

Dear How to Do It,

I’m a recovering porn and sex addict. I’ve been married for 14 years. Most of that time, my wife has had the pain of what I’ve done to her, including cheating and using her for sex in a way that was not healthy. We separated for a while, and in our healing, have been back together for a year. We are having a hard time reestablishing a sex life, and she has suffered a lot of trauma due to my past actions. She is finding it very difficult to relax and enjoy herself. She has started counseling, and I have listened to her feelings about what she is going through. It is very clear to both of us that we need to take a step back and slow down in our sex life. One issue that we’re not sure how to handle is she has a hard time communicating during sex. I want to give her a method to tell me that she is comfortable (or not) without having to ask her 1,000 questions, which also makes sex hard for her. The last thing I want is for her to freeze in the moment and me to think everything is fine. Do you have any communication techniques?

—Tentative

Dear Tentative,

Communication can be so much more than verbal exchanges. I imagine that after 14 years of marriage you have some grasp of your wife’s expressions, and can tell when she’s connected and when she’s checked out. Pay attention during sexual activity—if you see your wife cease to be engaged, you can stop and check in.

You can also establish a safe word, or a short verbal cue that sexual interaction needs to stop. They’re common in the BDSM community and can be useful in many situations. “Stop,” “red,” and “no” make great safe words—really, unless you’re explicitly incorporating themes of nonconsent, you should always stop when you hear these words. A more extreme possibility is having her hold something small, with the agreement that you’ll stop if she drops it. You’ll want the object to be heavy enough to notice when it hits the floor.

How is your wife with communicating after sex? I’m wondering if you could discuss the sex you’ve just had at whatever level of detail she’s comfortable with as a starting point. With practice, she might develop a stronger ability to communicate during sex, too.

Dear How to Do It,

I am a woman who, after 15 years of being sexually active, just learned how to squirt (!). Prior to this, I had only ever climaxed from clitoral stimulation, which sometimes takes a long time, particularly when I’m with a partner. I LOVE this newfound method for coming—it feels like a physical reaction to my arousal, whereas the clitoral method comes from more of a mental arousal for me. So now that I have the ability to become a geyser every day, I have a few questions for you, my favorite columnists.

1. I lose a lot of fluid so hydrating well seems key, but is there anything I should be aware of nutritionally?

2. It’s so messy! Do you have any recommendations for managing this besides laying towels down and doing copious amounts of laundry after, or finishing in the shower?

3. It feels like I’m really exercising my pelvic floor in a different way. My partner and I have talked about expanding our family in the next few years. This may be very wishful thinking, but has a person’s ability to squirt been shown to have any impact on childbirth—shorter/easier labor?

4. Is there anything else I should know? Any other insights would be very appreciated. Thank you so much!

—Old Faithful

Dear Old Faithful,

I talked to Amir Marashi, a New York–based gynecologist. He said he wouldn’t worry about getting dehydrated or losing nutrition from squirting, but that “whether you squirt or not, it’s a great idea to drink plenty of water”—good advice for us all. On pelvic floors, Marashi told me, “Exercising the pelvic floor muscles is very important and definitely helps you have an easier labor, and also after delivery, you will bounce back to your baseline much faster.” But maybe unsurprisingly, it doesn’t sound like squirting and labor length has been studied.

For managing the mess, you can also invest in a high-quality mattress protector or an absorbent throw like the ones Libidex makes. But towels are definitely a good way of managing the volume of liquid—you might keep a stack next to the bed—and moving your activities to the bathroom is another fine tactic. You can also always choose not to orgasm every time if you don’t want to deal with the mess.

Enjoy the fun new trick your vagina has learned! And remember, always carry a towel.

—Stoya

More How to Do It

I’m a 35-year-old married mother of two small children, and I’ve never had good sex. None of the men I was with when I was single in my 20s were interested in learning about the clitoris. Neither is my husband. I used to think that women who cheated were being ridiculous because the only thing I’ve ever gotten out of sex is ego gratification. But recently I’ve begun to think that this may not be all straight women’s experience of sex, and maybe some straight women cheat because they’re having orgasms with their affair partner. I want that. My question is whether it’s worth it to try to have an affair. For me, sex has always been all risk and no reward. I have become deeply cynical in this area. But there is a little tiny sprig of hope that makes me wonder: What if some men are interested in the clitoris and understand how to operate it? What if I can have an orgasm with someone else before I die? That reward would be worth the risk.