My Wife Wants to Put Some “Restrictions” on Our Next Threesome. This Is Totally Unfair.

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

Dear How to Do It, 

My wife and I are fairly adventurous in the bedroom, so a couple of months ago, we decided we wanted to try a threesome. After a fair amount of conversation, we agreed to invite another man to play with us. I initially had some misgivings, but after the experience, those dissipated. We both enjoyed it so much that we recently started planning another.

This time I asked if we could invite a woman to join us. My wife agreed, but with stipulations about what activities were permissible for me. Basically, she doesn’t want me doing anything other than watching or giving/receiving manual stimulation. This is totally unfair! She had no such restrictions the first time. I really want to pursue the threesome with another woman; it’s one of my fantasies, but I also don’t want any restrictions that might prevent me from enjoying anything our new playmate feels comfortable doing. Any suggestions on how to broach this topic with my wife without ruining my chances?

—Threesome Trouble

Dear Threesome Trouble,

Your statement that “This is totally unfair!” in the context you describe suggests a flat, tit-for-tat idea of fairness as equality based on exact sameness. This is at odds with reality. We are dealt different starting hands at the card table of life. Even identical twins, with the same genetics and raised together in the same nuclear family, tend to have at least one profound difference in their life trajectories in measurable ways (health and mental health conditions, career choices and success, and relationship outcomes). In the case of this disagreement with your wife, you each have different boundaries and requirements around protecting those boundaries. You seem to have proceeded with the threesome with a man without negotiating any guardrails on what would happen during the encounter, while your wife has chosen to require certain terms before she consents to a threesome with a woman.

On top of that, what a potential threesome-mate might feel comfortable doing is almost certain to be informed by the context of you and your wife as individuals, and your relationship as a pair. Meaning that while a woman who is happy to unicorn for a straight couple might be happy to have penetrative sex with both partners in most scenarios, having any kind of sexual interaction when discomfort or resentment is radiating from one or both partners is likely to be unappealing. If the chance you’re concerned about ruining is that of having a joyous romp with your wife and a third, and returning to blissful coupledom when you’re finished cleaning up, the biggest risk you could take is to debate and convince your wife into a sex act that she has qualms about. The other woman will almost certainly notice the tension, your wife will be unhappy, and you will have a hard time garnering sympathy from anyone in possession of all of the facts who is not also deep into the manosphere.

On the off chance that you have any mental health factors going on that tend to keep people entrenched in superficial black-and-white thinking, seek out support from a therapist who can help you work through that. Otherwise, try to understand why you’re bringing such an immature stance to this negotiation between your wife and yourself. Once you’ve figured out what’s making the discussion difficult on your end, ask your wife to help you understand her emotions, concerns, and boundaries, and what the limitations she’s telling you she needs are there for. When you have that information, you’ll be better positioned to understand how this first threesome with a woman can be set up to go well, and it’s very possible that your wife will be open to more flexible encounters later.

Dear How to Do It,

My lover (if that’s the right word) is a sensual woman who, due to vaginal pain issues, is averse to penetration and, due to emotional issues, averse to kissing on the mouth. The absence of both of those activities is quite frustrating for me. She is fully satisfied by my oral sex on her, and she usually manages to assist me in reaching an orgasm, but she is not what you’d call enthusiastic or highly engaged about it. The standoff gets more frustrating by the day. Thoughts? Ideas? Suggestions?

—Standoff in Hollywood (he/him)

Dear Standoff in Hollywood,

How frustrated are you? If the answer is a moderate amount, address this now. If you’re medium frustrated or more, find a way (journaling, talking with a friend who will protect your privacy, etc.) to work through those feelings so you understand what’s happening emotionally before you have the necessary conversations to address it.

You describe your lover as sensual, but of the activities that are possible for her, the only one she seems to enjoy is receiving oral sex. You need more certainty about what she enjoys and what she’s merely tolerating. From there, the two of you can consider whether there’s actually enough overlap between the acts both of you want to engage in for this to be a fulfilling sexual relationship, and whether either of you (I know you’re strongly missing penetration and kissing on the lips) is unable to experience anything that you require to feel satisfied.

Presuming that lovers is the accurate term for your relationship (and gosh, I wish I knew the story behind your own parenthetical there), the whole point is enjoying each other’s company in a romantic and delightful fashion. Lovers often connotes the same amount of expectation of emotional support as friends-with-benefits (in which the word “friends” mostly seems to set people up for disappointment). You haven’t made the kind of commitments, or built your lives around each other, in ways that require weighing economic and familial ties. If you reconsider your word choice and decide you’re in more of a significant relationship, you do need to weigh that when making your choices, but I’m taking what you’ve written at face value. When lovers are finding themselves going through the motions with each other, or harboring resentment, the question is not so much “How do I come to terms with the compromise required?” as it is “Can we find a middle ground that is erotically enjoyable for both of us, and, if not, how do we respectfully mark that the end of our time together has arrived?”

Have that talk respectfully, with extra caution around the penetration and kissing that your lover isn’t able to participate in, and get it sorted or move on before one or both of you is miserable, or your resentments become destructive.

Share Your Story With How to Do It!

Readers often have great suggestions for our letter writers, occasionally disagree with a point our How to Do It writers make, or simply want to provide some additional advice. Each month, Jessica and Rich will be replying to some of these comments and suggestions from readers. Write to us!

Dear How to Do It, 

I am struggling to masturbate because my clit has gotten bigger due to hormone replacement therapy (HRT). While I am super happy that it’s bigger, it’s not big enough to hold/pump, but it’s big enough that I can’t rub/DJ it. I would take another route, but insertion doesn’t do anything for me. Any advice?

—Butterfingers (he/him)

Dear Butterfingers,

Some vibrators known as “clit suckers” have openings that are on the wider side and might be enjoyable. Using a circling motion around your clitoris with the side of your finger (as opposed to the pad on the tip or bud of your clit) to stimulate the new length seems worth a try. Use plenty of lubricant, as you would for rubbing. Consider revisiting grinding and other techniques that are less focused directly on your clit and more dissipated in terms of pressure and motion, too. If you do best with concrete visual examples, dig through queer solo porn that features assigned female at birth folks who are on testosterone, or straight-marketed solo porn of cis women with larger clits, until you find people with anatomy similar to yours and then look at what they’re doing. Mostly, though, approach this the same way most people figured out how to masturbate in the first place, which is to start touching parts in different ways and make note of what feels good, great, and fantastic.

—Jessica

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