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 am engaged to a wonderful man—“Matt”—but don’t know how to handle my future mother-in-law “Janet.” She is an aging flower child, who is very open about her sex life and multiple boyfriends. At first, I thought this was funny and charming, but she is starting to get interested in my sex life too.
For example, she invited me to the public pool recently. When we were both undressed, she complimented the shape of my ass and speculated that Matt “must love to hold it.” Then she pointed out my neatly trimmed bush and suggested that I get completely waxed like her. She even invited me to feel how soft her hairless labia were! I am not a prude, but I am a very private person. I would feel uncomfortable with a close friend asking me to touch her private parts, much less my future mother-in-law.
I brought this up with Matt, who was completely mortified but didn’t want to intervene. He said that I should take Janet’s behavior as completely benign and loving, but try to hint that I am not as open about my body as she is. I have tried subtlety before, but she seems to be immune to it. How can I get Janet to back off without grievously offending her?
—Don’t Want to Touch
Dear Don’t Want to Touch,
You should slowly escalate the bluntness of your response when she crosses your boundaries again. There’s a chance that you’ll offend her. But there’s also a chance that being offended is the only thing that will get through to her. Your existing feelings of discomfort are more important than her potential offense.
Think about what you might say to Janet the next time she goes past what you’re comfortable with. Maybe: “I’m a very private person and am uncomfortable with this.” Or something like, “We’re past my boundaries here. Please turn the sexual volume down.”
You can also have a conversation before Janet makes another comment. You might start by acknowledging that the two of you have very different levels of openness around sex. If she agrees with this statement, have a bit of discussion about that. If an opening in the conversation doesn’t appear naturally in a few minutes, broach the subject of your comfort level regardless. I’d like to see Matt give you more support as well. He should, at least, be giving you useful tips on how to talk to his mother. Good luck.
Dear How to Do It,
My husband and I are both in our 50s and have been married since 2007. We have a fantastic relationship. We communicate, care for each other deeply, laugh, and talk about everything. But we do not have sex. In fact, we haven’t had sex since before we married. Recently, I brought this up and he confessed that he was worried that it would change the dynamics of our wonderful relationship. I told him that I felt that as long as we continue to be open and communicate, it shouldn’t so we agreed that we would do it.
The trouble is that neither of us knows how to start the process of doing it! We both agreed that we don’t want it to be at a set time. We want it to be more organic but the trouble is that it feels so awkward. We don’t sleep in the same bed, and I suspect that doesn’t help either. When we had sex previously, it was pretty marvelous and he even agreed that we had a very good sexual connection. I thought about wearing something a little sexy while getting ready for bed as a hint, while we are chatting and brushing our teeth, but I don’t want to come across as too aggressive. Any suggestions?
—Want to Do It
Dear Want to Do It,
Have another conversation, this time about what might and might not feel too assertive on your part. You can make your own yes, no, maybe list. Here are some ideas to get you started:
1. Wearing sexy clothes
2. Climbing into each others’ beds at night
3. Massage to see if it becomes erotic
4. Taking a bath or shower together
5. Talking about sex in an erotic way
6. Kissing for eight minutes
Both of you could come up with more of your own, and start a discussion of what seems likely to be fun or overwhelming. Your partner may have ideas they’d like to contribute. You can also read or listen to erotic stores for ideas, together or on your own. I think you’ve got this.
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Dear How to Do It,
I am in a nice relationship with my girl for two and a half years. Our sex life is pretty amazing with long sessions (45-60 minutes) four to five times a week. We are in our early 30s. I usually get turned on by hot women in the gym, walking outside, in a restaurant, etc. I don’t stare at them or want to have sex with them, but I usually let my sexual buildup ‘loose’ on my girlfriend.
I don’t think of other women while having sex with her apart from a momentary image in my mind here and there. It’s not like I don’t get turned on by her. Whenever we are together, we have sex as we don’t live together. I don’t masturbate (she does) but I do look at hot-bodied women once in a while on my Instagram (usually workout videos). I don’t actively search for pictures of other women on the internet.
Is that healthy sexual behaviour? It’s not that I even think about cheating on her. I don’t imagine having sex with other women. I just get turned on by some people (always physical attributes) sometimes and then come to her. I am confused because one of my friends says I am not physically attracted to my girl that much if I am getting turned on by random people.
—Innocuous Turn-Ons
Dear Innocuous,
Your behavior, as you describe it, sounds perfectly healthy. Many of the things you described yourself as not doing—masturbating, wanting to have sex with other women, searching for erotic images, or imagining having sex with other people—are also healthy expressions of sexual energy. And, even if you did engage in any of those actions, the only question that needs to be answered is whether you feel physically attracted to this woman who you’re having lengthy and regular sexual interactions with. I feel safe assuming the answer is yes.
If your friend brings it up again, you can tell them it isn’t that way for you or directly ask them to drop the subject. Enjoy your relationship.
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Dear How to Do It,
I’m a trans woman married to a cis man and I love our sex! I’ve always been a big fan of oral sex and have recently worked on anal sex (something I hadn’t done since high school), as well as participating in intercrural sex. My husband seems to love it no matter what kind of sex, which is a relief because I do, too. My only issue is that I’m having trouble with orgasms and cumming.
I’ve been on HRT for five years and, as a result, when I orgasm from masturbation (or any stimulation to my cunt) I don’t really cum. Instead, anywhere from 30 seconds to a few minutes afterward I’ll leak a clear, viscous precum-like substance (it’s annoying). That’s not the biggest issue, though. My husband won’t suck or lick my cunt and I’ve grown to be fine with it, but the only way he’s managed to make me cum since I started HRT is to finger me (whether that’s stimulating my prostate by rubbing my perineum or having his fingers actually in me) while I jack myself off, which I genuinely do love, as the act of being fingered gives me gender euphoria, weirdly! The problem is his arm and fingers get tired easily and I take a while to cum due to my hormones. He has expressed a desire to make me cum while he’s inside me, but I’m taller and larger than him so it’s pretty difficult to have him stimulate my genitals during penetration. This is further an issue because I have received an offer from my doctor to be referred to a bottom surgeon.
I’m interested in seeking out a consultation and potentially having a brand new pussy installed, but I’m worried I might never cum again if I do. It’s actually one of the biggest things keeping me from confirming a consultation. Do you have any tips for how we could get me to either cum faster or, alternatively, tips for how to cum during or from penetration?
—Trouble Finishing
Dear Trouble,
I reached out to Lucie Fielding, therapist, sex educator, and author of Trans Sex: Clinical Approaches to Trans Sexualities and Erotic Embodiments for her insight, and she has several specific recommendations:
“Before jumping into your question, I have to say: go you! I love that you love the sex you and your husband have and it sounds like y’all communicate well and are open to experimentation. But onto your concerns about cumming during and/or from penetrative sex…
Unfortunately, it would be hard for me to determine if there is a reliable way you might cum faster. But I do have a few ideas for some things you might try, ones that would also perhaps relieve your husband’s wrist/fingers and allow you to experience additional stimulation during penetration: First, you might try adding in some vibration. My personal favorite vibe is the Volta from Fun Factory, which has a ton of speeds/patterns and can deliver yummy stimulation to the glans (or whatever name you use for your parts), the perineum, or your external gonads. But most toys that are good for external stimulation of glans clitorises will do the trick! An added benefit is that you can hold the vibe to yourself while your husband is penetrating you anally. Double the sensation, double the fun. Second, to assist with wrist strain, sometimes a shift of position can do wonders, so propping yourself up on a firm pillow or a wedge can allow someone fucking you to experience less fatigue and strain.
Y’all might also try muffing. Muffing is a sex act that involves penetrating the inguinal canals of folks with external gonads. Described in great detail by Mira Bellwether in her indispensable zine Fucking Trans Women, muffing is another form of fingering that might feel equally gender euphoric for you and potentially bring a ton of pleasure. As for other suggestions for anal play, you might try butt plugs or other insertables (always with a flared base). And analingus can be a really good way to “wake up” the pleasure potential of that part of the body and get yourself good and relaxed.
As for your concerns about bottom surgery: I hear and validate those concerns! No one can promise particular forms of sensation, but I can say two things: Most surgeons do their best to preserve as much nerve function as possible in creating a new pussy. Sometimes sensation is elusive just after surgery but with proper and consistent post-surgical care, patience, and a willingness to swan dive into the awkward, it often returns.”
The function of a flared base or T handle on an anal toy is to prevent the object from going adventuring through your intestines, just FYI, so ask yourself whether the flare is extreme enough before inserting it. And, speaking of journeys, enjoy yours as you continue to explore your body.
—Stoya
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