‘Can He Come Inside Me During Anal?’ and 4 Other Burning Sex Questions, Answered



No matter how sexually open or educated you are, it’s a life truth that sometimes in the bedroom, weird shit goes down and you’re not quite equipped to deal with it. Sometimes it seems like these things should be simple enough to Google and find an answer, but doing it just makes you feel more confused. Whether it’s an mortifying question about bodily functions you forgot to ask your gynecologist, or an awkward situation you ran into with your partner, sometimes you just need an expert’s input on your sex life.

That’s why we’ve enlisted clinical sexologist and couple’s therapist Dr. Eve, author of the bestselling book Cyber Infidelity: The New SeductionDr. Eve wants women to raise their hands in the bedroom and tell their partners exactly what to do to get them off. And she wants you to be safe and happy while you’re doing it. Her years of training and expertise make her exceptionally qualified to advise you on the most intimate part of your life.

Below, Dr. Eve answers five burning sex questions. To submit yours for next month, email wtf@stylecaster.com.



Q: Is it OK for my boyfriend to come inside me during anal?

A: The short answer is no, it’s neither healthy nor safe. Think sexually transmitted diseases. Think pregnancy. Here’s how it happens: Semen has a sneaky way of slipping out one orifice and into another. The distance from the anus to the vagina is about a centimeter away. It takes the right time of month, no contraception, and one fast swimmer to make a baby. The notion that anal penetration is a sure way to avoid pregnancy is a myth that needs to be detonated.

Now, let’s go back to HIV, AIDS, and STI’s. Uncovered anal penetration is the number one sexual activity that carries the highest risk of infection. A penis thrusting into a tight dry hole that is contracting and resisting rather than expanding and inviting, is very likely going to cause the skin to tear. Ejaculation from anyone who is infected easily enters this broken skin and voila—an STI is passed on. Unless your partner has been recently tested and you know he’s clean—and even then, there really aren’t any guarantees; people cheat—your mantra should be: No glove, no love. Condoms and anal lube are non-negotiables with anal play. Reassure your guy that it’s not a matter of mistrust, it’s a matter of comfort and a way to ensure safe and healthy anal play.

By the way, keep condoms on hand because if you enjoy anal as well as vaginal penetration, you need to change condoms when you switch orifices. The last thing you want is bacteria being moved from one hole to the next!

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Q: How come my boyfriend can sometimes feel my IUD when we have sex, but not always?

A: First, a quick anatomy refresh: An IUD is inserted inside the uterus, via the cervix. The cervix is two to three centimeters long and connects the vagina and uterus. The average vagina is three to four inches long and can expand like a balloon by about 200 percent—seriously—when you’re turned on. The average erect penis is about 5 inches long. Mother nature likes symmetry and anatomical jigsaw puzzles.

So, the IUD sits inside your uterus and has strings hanging into your vagina to ensure your health care provider can remove it when you want to. You’re supposed to feel the strings when you reach your fingers deep inside your vagina. And in turn your boyfriend will also be able to feel these strings. But because your IUD can shift slightly in your uterus depending on your cycle, he might not feel them every time. If you have pain or discomfort related to this, be sure to reach out to your health care provider, since your IUD should not inhibit you nor your partner sexually. Try different positions until you find one that’s comfortable for both of you. When you’re really turned on, your vagina will engorge, and no strings will be felt.

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Q: Are uncircumcised penises less hygienic?

A: Imagine the folds of your genitals. They are interesting, and get more interesting as you unfold them and discover different sensations. You know when you shower, you need to unfold and uncover each part, and wash each part with warm soapy water. The same goes for uncut penises: Men need to give each part hygienic attention. It takes a little more time for uncircumcised do a daily clean. Moisture can get trapped between the penis and the foreskin, and bacteria love warm, moist places.

Sexually transmitted infections, specifically HPV and HIV, are more easily passed on by uncut men—hence the extra need for attention to genital hygiene. There is no definitive research that says women have more or less sexual pleasure with cut or uncut men. In terms of men’s own pleasure, unfortunately some men get circumcised in the hope it will delay their ejaculation—which is not always the best idea, given that some men report enjoying the extra sensitivity they feel once cut, while others say they actually feel less sensitive without a foreskin. It can really go either way.

A few more tips for getting (and giving) better sex with an uncut man: Before oral sex, retract his foreskin so he can feel every sensation. Use lube when you’re giving him a hand job; otherwise the movement can be painful. Watch him masturbate and copy his tugging or gentle caressing of his foreskin. When in doubt, since some foreskins are sturdy and others delicate, ask him how he likes you to touch him.

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Q: I hate waxes but my partner loves me bare. Who wins?

A: Pubic hair is so personal. It’s also political, follows trends, and, as in your situation, impacts power dynamics in a relationship. Personally, I think lying with legs spread in front of a stranger wielding a hot pot of wax can be daunting, bizarrely intimate, and damn painful. Politically, from a feminist perspective, you know it’s your hair, your body, and your genitals; thus your right to determine how much or how little of it there is.

Trends is where it gets interesting. The media exposes us to all kinds of repeated images of smooth vulvas clearly visible in tight jeans,  bikini bottoms, and Victoria’s Secret panties—which then become idealized and normalized. If you choose to buck this trend and maintain your individuality by keeping your bush, good on you, I say!  However, your boyfriend has been influenced by these trendy images, and I’d guess porn has been his trendsetter. And if you watch porn, you know that “bush” genre is also popular for people seeking unusual-looking genitals at a time when bare, smooth Barbie-looking labia are the norm. In other words, his erotic cues are tuned into bare.

How you manage this depends on how much you value this man and your relationship. If you love one another, I’m guessing it won’t be a deal breaker no matter what you decide. Perhaps you’ll shave or wax for six months, and then go wild for six as a compromise. The higher the relationship’s value, the more likely you are to talk about it, get an understanding of why he wants smooth, and then decide if this is the place to flex your power muscles and push for your rights—or give up the bush.

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Q: We want to try a threesome, but I’m weirded out by doing it with a friend or a sex worker. Ideas?

A: Choosing a friend adds emotional complications. Sex workers offer a clean transaction, as it comes with built-in boundaries, but understandably it is not for everyone. I suggest you try online dating sites, swingers groups, even Tinder or Grindr. And I strongly recommend you meet socially in public a few times before bedroom antics begin to ensure everyone’s comfortable together.

I also suggest that as you start to explore consensual non-monogamy, you enter this brave new world with a firm agreement in place—and the “who” you’re going to jump into bed with is only one part of that. Some tips: Talk a lot about both of your motivations for wanting to open up your relationship. Most couples enter threesomes consensually to strengthen and eroticize their own intimacy, which means that you need a strong relationship to avoid risks such as cheating or discovering this was your partner’s cowardly way of ending your relationship.

It’s also important to accept that you don’t know how you’ll feel during and after the first time you have someone new in bed with you and your partner. Good communication before and after acts as a buffer to what can be deeply complex feelings. Be very clear on personal boundaries around your own levels of comfortability. For example, you may not want your partner alone in the room with your third invitee; you may ban and permit certain sexual activities; or you may not want any contact with the new person after the fact. And, because this can’t be said enough times, always use condoms.

Put this all together and be sure you both agree to the terms before moving forward. It sounds unsexy, but it’s what will keep the experience a positive one. And finally, know that you can say NO at any time—even when the third person is already in your bed.

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