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 a healthy 42-year-old male, currently single, and open and adventurous sexually. For the first time in a decade probably, I was caught masturbating by a neighbor who let herself into my discreet side yard looking for a missing cat. I won’t go into all the details, but she saw everything, including me cumming all over myself. She’s funny and sexy and was clearly not distressed by the sight. It was an incredible orgasm for me, noticing her staring at me with a wry grin just as I was about to finish.
I’ve never been particularly ashamed about masturbating and have long enjoyed showing off for partners. I was a little surprised by how much I loved being startled so unexpectedly, though.
The long and short of it is, I would love to safely explore getting off under such circumstances further, but I am not sure how to. I’m not interested in hurting anyone or getting in any trouble or doing any damage to my good career or name. Can you offer any suggestions for exploring this kink safely?
— Eager to Share
Dear Eager to Share,
I’m tempted to deprive you like you deprived me: What happened after she caught you? We fade out on you coming on yourself, which is I guess cinematic but too vague an image for my taste. I wish you would have shared your interaction after immediately after, since being covered in cum has a way of affecting the dynamic. My desire for this information is not entirely about wanting narrative resolution—I wish I had some indication how she behaved after she caught you, and whether she’d felt skeeved out. I’m not saying she should have been. Among the first rules of benign trespassing is when you go digging around other people’s property, you might just find them jerking off. I just want the full picture of what, exactly, you’re idealizing.
It does seem that the implied enjoyment in her staring and wry grin is what rang your bell, so perhaps a masturbation club/party would be for you. It’s going to be a lot easier for you to find a party of this sort that caters to men who want to do this with other men, but there are so called “Jack and Jill” parties for a mixed-gender clientele. You might find such events, or at least the opportunity to show off your dick-polishing talents, in a space for swingers (though navigating a swingers club as a single man might be tough). Of course, if being startled is part of the point, you’re not going to be able to coordinate that in its pure form, as being unsuspecting in this context is an impossible thing to cultivate. Roleplay with a game partner—perhaps even this neighbor, if she really did enjoy her discovery so much—is about as close as you’re going to get to that ethically. Just something to keep in mind as you pursue this.
Dear How to Do It,
I slept with my close friend’s/old roommate’s ex-boyfriend. They’ve been broken up for about 6 months, and she’s been seeing someone else (not sure if that matters). It started as a drunken accident but has quickly turned into much more than that. He and I really like each other and want to continue seeing one another. In doing this I lost a friend and am getting ridiculed by a lot of other friends. I’m giving myself space from him for a little bit to reevaluate. Is my friend overreacting? Am I being that shitty? I don’t think there’s gonna be any mending of the friendship at this point. I’m pretty sure she wants to punch me in the face. I want to keep seeing this guy but feel guilty about it. Do you have any advice?
— Sorry I Slept With Your Ex
It’s hard to say exactly how shitty you’re being without knowing certain contextual details, but I think it’s safe to assume that you’re being at least moderately shitty. Even from within the sexually freewheeling urban gay culture that I hail, wherein one can sleep with a friend’s current boyfriend and do nothing to disrupt any of the attendant relationships, it’s always safer to assume that friends will have issues when you hook up with their exes. Call it girl/guy code, call it irrational, but you can’t miss this possibility when engaged in Western dating culture. You can, of course, ignore it and hope for the best, but the best owes you nothing, and in fact, looks like it skipped your situation entirely while making the rounds. If you have the hots for a friend’s ex, a heads-up is in order if you want to preserve that friendship. Some people don’t! For some, love (or passion or just really hot sex) is either more important or distracting enough to take on priority status. You get swept up in that mindset, you face consequences. And that’s what’s happening to you right now.
I don’t think this alone makes you a bad person. I don’t think your friend’s ex is her property. I know that proximity fosters these kinds of connections. This stuff happens! But then so do reactions to the stuff that happens. You aren’t entitled to everything you want, and in this case, you’ve chosen this dude over your friendship as well as greater social standing. Maybe that’s not fair, but surely you realized it was a possibility. It seems a little early to know that your friendship is over, but if that’s the case, you should just keep seeing the guy. You’re into each other and, as far as this social circle goes, he’s all you have left. Love the one you’re with, as they say.
Dear How to Do It,
My husband and I have been together for 25 years, married for 23 of those, and we have had our ups and downs as a couple. About two and a half years ago, I started a sexting relationship with a friend from high school. We live far from one another and didn’t really have the opportunity to see one another. A couple of months into this, I was feeling a lot of distress managing my relationship with my sexting partner and told my husband, who was not only understanding, but accepting, and pleased that my sex life with him had improved dramatically since my sexting relationship began.
A few months ago (over two years into our sexting relationship), I had the opportunity to see my sexting partner. My husband and I had a talk about opening up our relationship and we set some boundaries. These were to always wear protection, don’t get involved with mutual friends or people from work, AND he doesn’t want to know about any sex I might have with other people. I initiated the conversation as a way for me to seek permission to see my sexting partner. I did see him, we spent a couple of hours together, the sex was limited (oral), not entirely satisfying (although I very much enjoyed being with him), and I came home to my husband with a new appreciation for our healthy and robust sex life and his openness to allow me to have this experience.
Fast forward a few weeks, my husband was away and met a woman at a party. She came on to him, and he told her about our arrangement. Long story short, he proposed a threesome with myself, him, and this woman. She lives in his hometown, where he travels a couple of times a year. She is bi, but prefers women. I have often fantasized about being with another woman and roleplay it with my sexting partner pretty frequently, but I am fairly certain I’m heterosexual. This is the tricky part: I feel manipulative for seeking my husband’s blanket permission to have sex outside our marriage with someone I was already in a relationship with, but I’m not really interested in having a threesome with him and another woman. This is all still pretty new to me. I maintained the boundaries of our open agreement, and his ask is quite different from mine. How do I navigate this?
— Confused, Overwhelmed, and Probably Straight
I agree that his ask is quite different from yours, so try to let go of the false equivalency bubbling under your words. Just because he gave his blessing for you to make your sex texts real doesn’t mean he automatically gets what he wants of you sexually. You don’t owe him one.
Disabuse yourself of tit-for-tat logic. Your particular case, in fact, illustrates the shortcomings of thinking that way—just because you like one thing in bed (sex with a new dude) doesn’t mean you will like another completely different thing (sex with your husband and another woman). That’s a no-brainer.
The behavior that you describe, on your part, does not strike me as anything approaching manipulation. Hopefully there is nothing on his part that’s serving to convince you of this. (That would be manipulation!) If you really want to do your husband a solid, recuse yourself and give him the same blessing to pursue this woman that he gave you. But you don’t even have to do that! Every unique sex act and scenario is worth considering on its own terms and determining your comfort level with it as such. When you start getting into enforced obligation is when the open relationship starts to feel less like fun and more like work. Avoid that dynamic if you enjoy the feeling of temporary freedom.
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Dear How to Do It,
My boyfriend and I have recently gotten engaged after dating for over a year, and we’re planning on getting married next summer. We have sex weekly, usually when I stay at his place since he has his own apartment, and I have a roommate. He’s more comfortable with it at his place since it seems like he is a little hung up on having my roommate know/hear that we’re having sex.
The thing I’m asking about is that it’s never really come up that I also have toys that I like to use. And since we normally have sex at his place, there really hasn’t been any opportunity to bring them into our sex play, and he has never asked about it or brought one out. And I have both a big dildo and a couple of vibrators that I like using when I “feel an itch” to scratch. The dildo I use is very much on the big and thick side, and he’s pretty average-sized—I am not complaining about that at all—and I do wonder if he would freak out if he knew about it. He’s not super adventurous when it comes to sex; he’s never even brought up anal (and also see “hung up on my roomie hearing us”). I really feel like if I these toys out he would immediately feel like I’m making comparisons with him. But I kinda do like my “alone time” sometimes for some self-love.
Any ideas on how to plant the seed and make it seem like it’s his idea to add toys to our sexy time?
— Toys Are Fun
Dear Toys Are Fun,
Do you have any indication that your boyfriend will indeed think you’re comparing his dick (and commenting on his literal shortcomings) by producing a much larger slab of silicone? Or is that something you’ve invented and decided may be true, a pure case of projection? If it’s the latter, just have a brief conversation saying that you’d like to play with your toys with him some time and then bring them along. Don’t make a big deal about the big (fake) dick. Just play it cool. He’s not necessarily going to get insecure about a dildo, and anything that you can do to avoid sowing those seeds of insecurity will benefit you both. If he does get upset, just assure him that the dildo does not represent your views of ideal anatomy, it’s just a toy you enjoy. Sometimes a dildo is just a dildo.
If, on the other hand, he has given you some kind of indication that makes it clear that the presence of your little friend is going to cause a disruption, maybe leave that one at home, reserved for your me-time. You can’t always have everything you want in bed with your partners, and keeping things simple may save you both grief.
More How to Do It
I have been married to my wife for almost 20 years. It was a second marriage for both of us. A year into the marriage, I contracted an STD and found out she had it since her teens. At parties with her friends, I started hearing about how promiscuous she had been in her younger years, and I just accepted that it was before me. We have always had a real good sex life and discussed how great it has been, but now, she wants to practically stop having sex. I’m handsome, in great shape, and a very understanding and sensitive lover. She is still beautiful, attractive, and has no serious medical conditions. She explains that she had so much sex in her teens and early 20s that she can take it or leave it. In this case, it’s leaving it, and being the person who married her, I am now starting to pay a price for her early wild times. Is this a common rationale for writing off sex?