Roe: How Not to Set Up a Threesome, and Hooded Clits

Dear Roe,

I’m a 33-year-old woman and I’ve been with my boyfriend for over four years. I’ve known for years that he has always wanted to try a threesome with another woman, and I feel like we’re at a stage in our relationship that I would be comfortable doing it without feeling insecure or jealous. He’s friends with a woman who is very cool and open-minded about sex, she’s quite attractive and she’s single at the moment.

I don’t know her as well as he does, but we’ve met several times and she’s lovely and we both thought she’d be perfect. He’s spoken to her about our relationship and said we were thinking about trying a threesome, but he never explicitly specified that we were thinking about her, and she was encouraging him to try it.

We wanted things to feel very organic so we invited her over for dinner and he started flirting with her a bit. However, she either wasn’t into it or wasn’t getting the hint and left soon after. My boyfriend has texted her since and she seems fine but we haven’t hung out since, and we’re worried that we pushed her away or scared her – or that we’re going to have to have an awkward conversation with her if we want to have a threesome with her. Did we breach threesome etiquette in some way, and should we try with her again?

Dear Letter Writer,

Goddamn, porn has so much to answer for.

Here’s what happened: you invited a good friend over to dinner, she ate dinner, she chatted, she probably wondered why your boyfriend was getting a bit creepy on her in front of you, blamed his third glass of wine and politely left. You know, like people do at dinner parties.

Your mistake here was believing the porn-created myth that threesomes just spontaneously happen, like trolling comments on an article on feminism, or black hairs on your chin if you’re a woman over 25. (That was a nice surprise – thanks, second puberty.)

Threesomes don’t just happen. Sure, I’m certain that at sex parties or at very drunken college parties one or two threesomes have just organically happened – but you’re in your 30s, this was a dinner party, and believe it or not, it is entirely possible for you to have thoughts that other people are not privy to.

This woman probably had no bloody idea that a threesome with her was on the agenda – because you or your boyfriend had never said so, despite apparently having some very natural openings in these conversations about your sex life.

But neither you nor your boyfriend suggested just asking her if she was interested. Why? Because you thought THAT would be “awkward”? More awkward than your weird agenda-laden appetizers? More awkward than actually having sex with her??

Like all sex, if you’re not ready to have the conversation about the sex, you’re not ready for the sex.

And like all sex, having a conversation beforehand and doing some planning will probably put everyone’s mind at ease and make the sex a lot more fun and enjoyable.

This rule particularly applies to threesomes, because everyone might have very different ideas of what is sexy, or allowed, and there are safety considerations that need to be addressed, as well as . . . oh, what was that other thing . . . oh yeah – you have to be sure the third party actually wants to have sex with both of you.

So whether you decide to try it again with this woman, or choose a different person, you and your boyfriend need to put on your grown-up pants and have a real conversation about what you’re thinking.

Have a drink with the woman, tell her that this is something you as a couple have been thinking about, and while there’s absolutely no pressure and you’re totally fine if she’s not interested, her name has come up, so you’re both wondering if she’d be interested.

If she seems hesitant or uncomfortable, drop it immediately. If she changes her mind, she can bring it up again, but you don’t want to be the couple who lose friends by pressuring them into sleeping with both of you.

If she does seem interested, talk through the basics: are there certain activities you want to keep just between you and your boyfriend? Have all of you been tested for STDs, and are all of your comfortable using condoms? Is she allowed stay over after? Is this a once-off bucket-list thing or if all goes well would you like it to be regular? Are you all allowed to tell other people if it goes ahead, or is it just between you?

Then I’d give her a chance to check in with both of you individually, just in case she has any questions or concerns she’s more comfortable sharing one-on-one.

Then, and only then, do you broach all going back to yours.

Grow up. Conversation first, then sex.

And for god’s sake, don’t have dinner right before sex. No one wants to fuck with a food-baby. Amateur mistake.

***

Dear Roe,

So this is a bit embarrassing. I’m a 26-year-old woman, and I’ve never found it very easy to orgasm. Having my clitoris stimulated with fingers (mine or my boyfriend’s) never feels like “enough”, but if I use a vibrator on my clitoris it feels like waaaay too much, more uncomfortable than sexy. I thought this was just a weird quirk, but I recently started going out with a new man and he remarked the other night that he found it hard to find my clitoris when giving me oral – not that he doesn’t know where the clitoris is, but that mine was literally hidden under . . . skin folds?? I don’t know what the term is, but it is covered, I have to pull back some skin to expose it, if that makes sense. I don’t know if this is normal (it doesn’t look normal), and if maybe this is why I find it so hard to orgasm. Should I be worried, or look into surgery to expose it more??

Dear Letter Writer,

My dear, you are in possession of a hooded clitoris. Mazel tov!

Actually, that’s a bit misleading – every clitoris comes with a hood, but some are just more prominent than others.

It sounds like the hood of your clitoris may cover it entirely, which is perfectly normal and definitely does not mean you need surgery. I repeat: you do not need to even consider surgery on your perfectly normal genitals.

Having a clitoral hood is normal. It’s kind of like the vaginal equivalent of a foreskin. And there’s a lot of variety. Here’s a (NSFW) link to a photography project illustrating the vast variety that clitorises and their hoods can come in.

So the question isn’t about normal/abnormal, because it is normal. The question is how to get the most amount of pleasure possible, and that means embracing how your body is made, not stressing about it.

And there’s much to embrace: because your clitoris is covered, it may actually be more sensitive than women with small clitoral hoods, because their clitoris is more accustomed to being rubbed by their underwear, jeans, etc, whereas yours has a bit more protection – which likely explains why direct stimulation feels uncomfortable.

So instead of looking to uncover and directly stimulate your clitoris, work with your hood. Try stimulate your clitoris through your hood – you may need slightly more forceful movement with a tongue/fingers to get going at first, and then slowly work up to pulling the hood back for more direct contact.

If using a vibrator, don’t apply it directly to your clitoris but allow your hood to act as the natural buffer it is, again allowing you to work up to what feels good. It may also be worth playing around with a combination of your fingers and vibrator to get used to different sensations – try putting your fingers over your clit, then placing your vibrator on your fingers, rather than your clit, allowing you to get the direct force and movement of your fingers, with all the delicious mechanized wonder of your vibrator.

As with everything to do with your pleasure, my advice is to play! Don’t put pressure on yourself to achieve orgasm, as the stress will undo the arousal. Just settle in for the night, with your boyfriend, vibrator or both, and see what feels good.