How to Do It

My New Boyfriend’s Penis Had a Big Surprise for Me

I need a plan.

A man contemplates a "thick" toliet paper roll.
He broke the “toiler paper test.” Photo illustration by Slate. Photos by 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’m having a lot of fun with my new partner, but there’s a problem I can’t quite wrap … my head around.

This guy has a very thick dick. I have a very small mouth. I would like to give him oral, but my teeth keep getting in the way. I’ve tried putting my lips over my teeth, but I can’t maintain that position. I lick and kiss his dick, but we would both like me to take him into my mouth. Is there an item that would protect his tender manhood from my teeth? Or do you have another suggestion to help with this beautiful curse?

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—Girth Grinch

Dear GG,

I wear a night guard because I grind my teeth. I have delivered at least one blowjob with it in, and found it just as easy as without a dental device. Presumably it will also feel better than your teeth. You probably don’t need one custom made for your mouth—unless you also grind your teeth, in which case I strongly suggest it for sleeping—but there are plenty of drug-store options. You’ll want to find one meant for smaller mouths.

Let me know how it goes, and if readers want to share their own girth-vanquishing tips via email, we’ll include your success stories on a future episode of the How to Do It podcast. (Subscribe now at that link—you never know what you’ll learn.)

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Dear How to Do It,

A while back, I was hooking up with this girl. She had some pretty extreme BDSM fantasies, and in general I was happy to play with her in that fashion. But she started getting into a fantasy where she played at being “raped” at knifepoint. I only tried it once. It was awful. Care always needs to be taken with BDSM, but when you have a bare Yawara involved, making sure I didn’t cut her in half occupied the overwhelming majority of my attention, which just made the whole experience an unpleasant task to get through. For me, anyway. She loved it. We argued about that, and wound up stop seeing each other sexually, although we still keep in contact as friends.

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Well, I recently found out she’s in the hospital—for a knife wound on her throat. Two guesses as to how she got it. She said she doesn’t appear to have any permanent tracheal damage, which is good, but I really think she’s slipped off the edge into wanting a sort of sex that could actually and immediately kill her. I’m not much more than a casual acquaintance these days, and I’m wondering what I could be doing to warn her about the extreme risks of her lifestyle.

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—Knives Out

Dear Knives Out,

Having just landed in the hospital with a sex wound, I suspect she’s quite aware of how risky her enactments of her desires are. And giving her a lecture is likely to drive her away. I’d check in on her general mental state. How’s she feeling about life? How are her social relationships? How is she handling this massive pandemic we’re all still navigating through? Is there any way you can support her self-care skills? Basically, how can you meet her where she is and help her feel good enough about life that it becomes more important than this one, deeply dangerous, sexual practice? There are probably limits to what you can do here, but starting there might help.

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Dear How to Do It,

My husband and I have been working through some marriage issues. One of those issues is porn. In the beginning of our relationship, porn use for either of us was not a point of contention. But not all porn is the same, and over time I have found that I feel threatened by some forms of porn—namely, social media and paying subscription fees to the artist. We have had several thoughtful discussions, and a couple not-so-thoughtful arguments. Ultimately, we decided to compromise by limiting porn consumption to a paid subscription on one of the major websites only, since it does not have any social capabilities.

However, I have gotten into a bad habit of disconnecting emotionally during sex and approaching it like a performance rather than a loving interaction. My husband and I decided that when I reached the point where I can no longer stay emotionally present, I should tell him and we should stop. Since then, sex has been inconsistent. We’ve had sex, but last time for example, after I said that I needed to back off (after making out and petting), he got up to watch porn in the other room. This was on the site we had agreed he could use, but spending time intimately together and then having him go back to porn triggered some of my insecurities, and I asked him to stop.

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I recognize that just asking him for foreplay without completion is effectively what I have been doing recently, and that is not sustainable.  We have been married 12 years. My pleasure and my orgasm are important to him, and his pleasure is important to me. He has bought me several toys, and he is attentive to my requests for pretty much any physical stimulation. I have no complaints regarding his technique or performance. However, we are missing a connection. Do you have any tips or suggestions for restoring emotional intimacy to our sex life?

—Missing the Romance

Dear Missing the Romance,

I think I understand your reasoning, but you wrote to a sex worker, and I feel obligated to mention that paying fees directly to the artist supports performer autonomy and self-determination—whereas paying for a subscription to a large website supports corporate control of sexual material and generally leads to homogenization and more aggressive sex or extreme power imbalances in scenes and on set. You might consider CrashPadSeries, MakeLoveNotPorn, or Lustery if you want to split the difference.

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Do you have any insight into why you’re disconnecting emotionally during sex? If you can figure out what’s going on there, you can see where you need to work on things. Are you missing a connection in other areas of your life together? If so, think back on how you initially connected—what did you do together, talk about, and see in each other? If not, great—you’ve got somewhere stable to build from. Are you having anxiety about sex? Then you might want to dig deeper and ask yourself what you’re anxious about. Is porn and your feelings about it the root of your problem? In that case, dismantle those insecurities—remember what you bring to the table and believe that your husband desires you.

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Your situation seems like one where short-term therapy could be helpful. If there’s room in your budget, look for a therapist with experience in sexuality, and if you aren’t finding any with that specialty listed in their bio, ask when you have your initial phone call. You also might have success with apps like Better Help or similar.

Dear How to Do It,

I‘m a young gay man who‘s just started dating now that I‘ve moved out. I‘m excited, but because of my inexperience with other guys as well as some past trauma, I’m also filled with dread, and I find there are times where I need to “pump the brakes” during intimacy because I realize I’m no longer comfortable being touched. Unfortunately, though, I experience a lot of anxiety telling guys “no,” as this would in the past lead to guilt tripping or physical violence from exes. I understand now that a respectful person would simply stop when asked, but it’s like my whole brain shuts down and I struggle to say what I mean—or honestly anything at all. This has put me in unsafe situations before, and I know I really shouldn’t be hooking up with guys until I get this skill down, but I don’t know even where to begin. Like, what’s the safest way to back out of a physical encounter that starts going wrong? Is there some way, non-verbally, that I can let a guy know I’m uncomfortable and need him to stop touching me? Or is there perhaps a “script” I can follow or phrase I can memorize?

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—Red Light

Dear Red Light,

I think your best bet is to give partners a heads up before you get into sexual interaction. Something like “Sometimes I freeze up during sex and need to stop suddenly. If I stop giving you active consent, like (insert what active consent looks like for you), I need you to disengage and give me physical space.” The way a potential partner responds to this will tell you a lot.

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You can also come up with a tactile hand signal. In the mainstream porn industry we used to tap the guy’s upper thigh as a way to signal “slow down” without stopping the action. Something that involves physical touch is useful because it’s more noticeable than a wave or finger wiggle, and you want to connect to a part of the body that you don’t normally touch during sexual activity so it’s clearly a communication. Safe words are another great solution. If you can get out “red” or “stop,” you can call for a coital cease.

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As for safely backing out, avoid your place for the hookups. Make sure a friend knows where you are. Keep your clothes in a pile between you and the door. Know where the exits are. You never know how a hookup is going to go, and it’s easier to leave in a hurry if you know where your belongings are and where exactly you need to head once you’ve got them. Watch what you imbibe, too.

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If a counselor is at all feasible for you, that’s likely to help as you work through this at first. Good luck.

More How to Do It

My husband and I have a pretty good sex life and communicate well, or at least I thought so. Last March, he became a bit more amorous, and our sex increased, which I attributed to working at home. I was happy to go along and it’s been a nice perk in our lives. Then I discovered what’s really going on by stumbling onto something on his computer—and I’m aghast at what I found.

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