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 32-year-old straight woman. I have never had sex. I don’t frequently masturbate, but when I do, it’s AWESOME. I’m cool with having an apparently low sex drive. But I want to have sex. I know what makes me feel good, I’ve discovered a couple of kinks, and I know what my absolute Do Not Want areas are.
The thing is, the area I live in doesn’t have the best choices for casual sex. I have several close male friends, but they are NOT options—I wouldn’t want to possibly screw up a long-term friendship, neither would they, and we’re more like siblings. I would also feel too awkward hooking up with someone who probably knows one of those guys, and would probably be douchey enough to tell them. That might make me too picky, but given my anxiety issues, it’s something I take into consideration.
Now I’m seriously considering saving my money and, post-COVID, taking a vacation somewhere that has legal prostitution and finding a male prostitute to do the job for me. My rationale is thus: They know what they’re doing. They won’t fight me on protection. And they might be more willing to indulge in my kink than a regular guy. Would that be a completely awful idea? If not, are there ways to do this properly that would give me the best chance for a safe experience?
—Paying Up
Dear Paying Up,
You sound pretty self-possessed about what you want, so I decided to focus on your second question. I was able to find a trio of male escorts who see female clients in Australia, where sex work is decriminalized or legal in many parts of the country. “Male escorts who see and provide sexual services for women are a far rarer commodity than just about every other kind of sex worker,” Cameron Hart, one such escort, told me. “In a very general sense, there is less demand and therefore a far smaller industry base with which to engage when looking for a suitable provider.” He suggested that you consider writing to female service providers for referrals: “Sometimes reaching out to other sex workers or providers (specifically women) to ask their opinion of or recommendation on male sex workers can give you an insight into how they conduct themselves professionally and in the sex work community. I know as a fact that many of my clients are referred to me by women in the sex industry.”
Escort John Oh also suggests that you do your research. “Read each guy’s website,” he said. “Get the best picture that you can of them. Then drop them an email and politely inquire if you can spend some time getting to know them. Offer to pay for their time to do so. I’m sure that you will figure out quickly enough if any given guy might suit you.” A third “professional companion,” Ryan James, said not to stop there: “After checking out their professional pictures on their website, have a look at their social media to find casual and recent pictures. Read through their bio and everything else you can find on their website about what they offer. Then go on to check if they’ve written anything elsewhere. See if they have a blog, if they’ve done any interviews. All this helps paint a picture of what they might be like in person and whether they would be a good match for you.”
All three of the men I contacted strongly encourage communication, particularly when kink is in the mix. “When contacting an escort, an email, text or phone call simply requesting what you’re after is all that’s necessary. Your name, type of service that you’re after, preferred date, time and location. Be sure to mention anything specific that you’re after, especially when it comes to kink,” James said. Hart echoed that: “Some of us are trained in specific kink protocol, whilst others are not—and this will often impact our eagerness to provide for specific kinds of requests or desires. As an example, I am happy to fulfill moderate BDSM fantasies and requests, but high-protocol kink and scenes requiring significant skill I will often refer out to other providers who I know are trained, skilled and well regarded in that area. Again, the best way to assess whether a provider is right for you is to reach out and communicate.”
Both Hart and James cautioned that a provider asking for a picture of you is a red flag, and asking for sexually explicit images is a whole red parade. Another red flag is if they send you sexual images without asking for your consent first.
So I think your best bet is to start looking now, while you’re saving, to get an idea of what services and which providers might be interesting to you in whatever destination you decide to go with. Hart also said to consider first patronizing sex workers digitally via subscription platforms, and I think that might be a useful way for you to practice communicating with a provider. “You should never be afraid to reach out, whether that be by email, Twitter message, or even a private message through OnlyFans (or whichever platform the provider is using). Most of us are more than happy to discuss private or personalized content creation with fans or clients,” he said.
And as I always advise for safety when meeting someone new: Meet in public first, tell a trusted friend where you’re going, and set check-in time(s). You don’t necessarily have to mention every last detail. Best of luck.
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Dear How to Do It,
I’m sure if this even counts as a “problem,” but I’d appreciate your thoughts on something. My wife and I are in our 50s. Third marriage for both of us. We’ve been together 10 years, and married for six. Our sex life is amazing, for our age but also for most any age. We make love virtually every day; if we happen to miss a day (tired, not feeling the best, ate supper too late), we often have sex twice the next day. Usually there is no “initiator”; it is just understood that we both desire each other whenever the opportunity arises. Afterward, we cuddle blissfully, sleep soundly, and wake up happy. So, here is the question: Most of the time, my wife prefers to have intercourse and that I have an orgasm, but she only wants to have an orgasm occasionally, usually once a week, and only after she has taken a very long and thorough shower. (She only orgasms with oral sex.) I’d love for her to orgasm more often, and would happily go down on her anytime, anywhere, with or without a preparatory shower. What should I do? Is this even an issue? Should I just count my blessings and carry on? I’ve tried several times to talk about this. She admits she has a bit of a self-consciousness issue about cleanliness, how she smells “down there,” etc. I’ve reassured her that I’m not squeamish, and that in any case she is super hygienic. But clearly the discussion makes her uncomfortable, so I drop it. Any thoughts on a different approach? Or should I just accept that this is the way she wants it and carry on with our perfectly wonderful sex life?
—No Qualms
Dear No Qualms,
I think valuing the female orgasm is generally good—very good—but in this case, you may be overvaluing it. Remember, sex is about the journey. The experience. The intimacy. Orgasms can be nice, but they don’t need to happen in every sexual interaction. It sounds like your wife is very satisfied with the sex the two of you have, and doesn’t need or want to orgasm every time.
It’s less about your squeamishness and more about hers. She doesn’t feel comfortable receiving oral sex unless she’s had that shower. You’ve brought it up multiple times and say that the discussion clearly makes her uncomfortable. Respect her boundaries and leave it alone.
Dear How to Do It,
I’m a 36-year-old man living in a major city. My girlfriend and I have been dating for about three years, and we decided to have an open relationship for the past two years. This was my first open relationship, and my partner’s second. We stopped that after the pandemic hit, and now we’ve had some time to talk and reflect about the last couple of years.
We set some ground rules: honesty, safe sex, etc. My girlfriend typically hooked up with someone once every two or three months. The problem is that in the last two years, I’ve struck out every single time. I know that it’s easier for women to hook up than it is for men, and it’s not about keeping score, but I’ve had ZERO hookups! When I was single, I never had a dry spell like this. The problem is always the same: I meet someone online (Tinder, OkC) or in person, and it seems to be going well at first. I’m able to get a reply or a date pretty regularly. Early on, I’m honest with the fact that I’m in an open relationship, because I don’t want to deceive anyone. This immediately puts up a wall, even if I thought it was clear from the start that it was a casual encounter. Every woman I’ve met does not want to have a casual encounter with me because I’m in a relationship, even when I tell them it’s open and my partner knows.
Is this a normal experience for men in open relationships? How do you get around this problem? Do I not tell the other person I’m in a relationship? This seems dishonest and could hurt them, which I absolutely do not want to do. My girlfriend is equally baffled. After two years of trying, I feel shunned and ready to give up.
—Great Wall
Dear Great Wall,
Open relationships are a difficult thing for many people to understand. Potential partners may be confused and not want to put in the energy and effort to understand your situation, in the same way that people who care for elderly family members or have children may struggle to find partners willing to wrap their heads around those complexities. Potential partners may be unsure whether everything is above board because they’re unfamiliar with the concept of non-monogamy or because they’ve been burned in the past.
I want to take a moment to applaud you for being direct and upfront about your primary relationship. I agree that hiding it would be dishonest and potentially set the prospective partner to feel hurt, used, or misled. Bravo.
I think you should put the fact that you have a primary relationship and are looking for hookups in your OKCupid profile in a pretty obvious way, to make the process more efficient. And I think that you might have a better chance of success on Feeld, as they cater to people looking for threesomes and non-monogamous hookups. You also might find success at poly munches or other sorts of meetups. You know, presuming that the COVID situation improves and you and your main partner decide to continue non-monogamy.
You don’t get around the problem so much as you push through the problem. You “keep putting yourself out there” until you find someone who is interested in what you have to offer, and then you foster that relationship to whatever degree you’re both comfortable with. Good luck.
Dear How to Do It,
My partner and I have been together for 15 years. We grew up in the evangelical church hearing “No premarital sex! Women’s bodies should be hidden! Sex is dirty!” and so on. It took us YEARS to even know how to talk about sex, and we’ve been each other’s only sexual partners (after marriage, of course). We’ve discovered that sex is actually pretty great, and talking about it helps—who knew?! But I’m stuck on how to broach non-vanilla sex. I have two main problems: One, I’m curious and want to explore, but I don’t know what’s even out there. Unfortunately, porn isn’t an option—I still have too many layers of guilt to work through before I could enjoy it. Is there a nice list somewhere with a bunch of the things people do and how to do them? Two, how do we talk about these “adventurous” things without it being awkward? My partner has always been loving and patient and supportive, but I feel like I’d be bringing up something gross or perverted (thanks church), and I don’t know how to get over that.
—Holy Union
Dear Holy Union,
Nadia Bolz Weber wrote a book called Shameless: A Sexual Reformation that I recommend to anyone raised in the Christian faith who is struggling with sexual intimacy as an adult. I thought it was wonderful. Some people find it too aggressively critical of conservative Christianity and the purity movement, but I think a read through will help you feel soothed by reminding you that you aren’t alone.
As for what’s out there, well, there’s a whole buffet. I’m not sure what vanilla means to you, so I’ll start simple. You can pleasure each other with your mouths. You can use your anuses as sources of salacious sensation. Stimulation of feet, particularly toes, can be another fun feeling. The main question to ask yourself in this department is: “What feels good?”
There’s a vast array of BDSM—bondage, domination, sadism, masochism—activities. This can be anything from light hair pulling or a couple of smacks on the butt, through one of you holding the other’s wrists with your hands, to elaborate scenes involving hours of rope bondage or scripted psychodrama. Are you curious about experiencing pain sensations? How about delivering those sensations? Can you imagine yourself in charge of the action? Do you want to submit to your partner’s whims? Do you want to be worshipped, put temporarily on a pedestal? Does physical restraint sound interesting? And physically restraining your partner? Do you have any fantasies you’d like to roleplay?
Sometimes talking about sex is awkward. Sometimes sex itself is awkward. Sharing our desires involves vulnerability. You might consider practicing—when you’re alone, in the mirror, saying “I’m still curious about sex” or “I want to try ______ with you.” Get a feel for the words in your mouth before you try to communicate with your partner. Another thing to do before you begin to communicate is reminding yourself of your history and the fact that your feelings are OK. “I feel shame around sexuality because of the messages I heard growing up. I know that shame doesn’t serve me, but it’s OK that I’m feeling it.” You might even start the conversation with your partner with this. “We’ve talked about the ways our upbringings have affected us. I believe you understand my apprehension. I want to explore the rest of sex with you, and I’m not sure how to talk about that.”
Take your time, be patient with yourself, and let your desires lead you. Good luck.
—Stoya
More How to Do ItMy wife and I have been together for many years and married only recently. We have a regular, healthy sex life that I would call vanilla with some extra toppings. We also are pretty open about sex and masturbation (hell, I surprised her with a new vibrator when we found her old one was dying out). But there’s one fantasy I haven’t told her about—and it has to do with her impending pregnancy. I really don’t feel comfortable telling her about my dark secret that when she is seven to nine months’ pregnant, all I’ll want to do is bone her.
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