How to Do It

I Thought Dating a Well-Endowed Guy Would Be Great

Uh …

A man hugging a woman.
Photo illustration by Slate. Photo by OJO_Images/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!

Every week, the crew responds to a bonus question in chat form.

Dear How to Do It,

I’m a woman in my late 30s. Until about a year ago, all of my relationships were with “average”-sized guys. About a year ago, though, I started dating a wonderful man who is also quite well-endowed (around 9 inches). This should be great, but he keeps hitting my cervix, which for me causes a huge amount of pain. Sex with us is also not as spontaneous as it has been with previous partners because it requires more lube, foreplay, etc. I also find it hard to give him a sustained blowjob because he’s also pretty thick and my jaw gets tired much faster than it has with previous partners. I’ve talked other female friends about this problem, and they are either envious or, if they have well-endowed partners, they don’t have the cervix pain that I do. I really like this guy (and he’s otherwise great in bed!), but I’d love to be able to actually appreciate his size rather than be annoyed by it. Do you have any tips?

—Big Trouble

Stoya: I’m going to blow my load early and start with my very best trick. Use your hand. Give him a reach-around, except instead of reaching around his body, reach around yours. If my hand is anything to go by, that’s about four inches of extra space.

Rich: So you’re literally creating a buffer with your hand that will prevent him from going too deep?

Stoya: Yup.

Rich: Do you have any experience with the devices developed to help this (and other issues that result in pain from deep penetration) such as the Ohnut or the ComeClose Pleasure Ring?

Stoya: Well, consider my mind blown. Please inform me about these devices.

Rich: They’re also buffers worn at the base of the penis, but the advantage here is that they would allow her the complete freedom of her hands. Basically, the sex-aid equivalent of that microphone headset Madonna had developed for the Blond Ambition World Tour. They can both be used to help in this very issue, a big penis hitting the cervix and causing “collision dyspareunia.” But these can also be used in the case of health complications like endometriosis. The Ohnut is highly adjustable, giving you a lot of inches to work with (or reduce, as it were).

Stoya: This is life-changing.

Rich: I’m glad to be of cervical assistance.

Stoya: I did spend the whole weekend wondering what kind of research you were going to come up with.

Rich: Haha, well … I did more. And it turns out that for some people, direct stimulation of the cervix is highly pleasurable and even results in its own distinct genre of orgasm. Not the case here—pain is also a common response. Just goes to show that every body is its own unique maze of sensations.

Stoya: As a cervix-haver, some bodies have both reactions, depending on the time of cycle and exact placement.

Rich: That’s interesting.

Stoya: For me, if the cock is in front of the cervix, it’s wonderful, and if it’s behind it, then I’m finished and need to curl up in a ball.

Rich: And does that mostly depend on the shape or curve of it, or can that be corrected with positioning?

Stoya: In my anecdotal experience, some men can correct with positioning and others are hopeless. It seems to depend on how in tune with their bodies they are, and particularly how sensitive their genitals are—how well they can feel where their penis is in vaginal space.

Rich: Well, that brings me to another point. While I do think your sexual health and pleasure is, for the most part, in your own hands, it’s kind of a bummer that she’s the one asking this question and not him. I feel like if you have a big dick, the one downside is you need to learn how to wield it. You get a bit more work as a result of genes smiling upon you.

Stoya: I can imagine it might be difficult to get honest feedback with the kind of nuance that helps one figure out exactly what spot to avoid? Like, when I’ve been punched in the back of the cervix, I’m definitely not on board for a “Does this hurt? How about now?” research mission. And it took me—the career sex worker!—until a couple of years ago to figure out what was an OK zone to a degree I could communicate effectively. BUT: I agree that it’d have been nice to hear from him, asking how to wield his enormous wiener.

Rich: It makes sense. Is there anything in particular that pushed you over the edge in terms of effective communication, or was it just a matter of general experience?

Stoya: It was the diva cup. It has to go way up in there, and then you have to squeeze it just right to get it sealed properly, so I spent a lot of time feeling around my cervix.

Rich: There’s really no substitute for that kind of bodily awareness. Do you think that lube or attempting to be in the highest state of arousal during penetration could help here?

Stoya: I don’t think lube is going to help the cervix issue. Heightened arousal might. It doesn’t for me, but that doesn’t mean anything for this woman’s body. I’m suspecting that he’s also significantly wide. Lube and arousal will absolutely help with accommodating girth.

Rich: Right “he’s also pretty thick”—which brings us to the blowjob question. I wonder what is to be done besides her best (with a heaping dose of hand action).

Stoya: She should discuss, and pending his approval try, all the three button moves: ball sucking, taint pressing, anal fingering. Those make for nice jaw-resting breaks.

Rich: And again, it would be wonderful if he’d weigh in. Having a big penis must at least give you some sense of what’s worked in the past to get you off. I mean, having any penis should?

Stoya: I’m wondering if there’s a world where he assists with his hand.

Rich: Seems like he’s big enough that if he’s at all flexible, he could assist with his mouth. I kid, but regardless, it’d be useful for him to step in and help out—that’s too much dick to task one person with handling.

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