How to Have Sex with Basically Anyone
Yes, Anyone!
I’m going to be 40 years old this year, and it’s the 20th anniversary of my involvement in the world of erotic labor. I’ve worked as a phone sex operator, (what a colleague lovingly calls the “phone bone”) a stripper, a nudie booth worker, an erotic model for private collectors, a performer and director for feminist porn, a pro-Dom, and more recently, a hands-on Intimacy Coach. I’ve also attended, given workshops at, and planned and hosted dozens and dozens of sex parties over the last 12 years. In my more mainstream endeavors, I’m a highly credentialed sexuality educator and have been teaching on topics related to sex, love, relationships, kink, and more for about the last 15.
Because I’m relatively pansexual (I don’t really have a genital preference and I have the capacity to be attracted to people of any gender) I’ve had sex with almost every kind of person you can imagine: trans, cis, non-binary, people with vulvas, people with penises, people who have transitioned with hormones, people who have had gender-affirming genital surgeries, people with disabilities, fat people, thin people, people of different races, two people at once, more than two people at once — you get the picture. My hands have touched hundreds of human bodies over the years in various capacities, both professionally and in my own personal sex life, with the aim of creating and sharing erotic energy and pleasure. I’ve enjoyed letting just as many hands touch me with the same aims in mind, and let-me-tell-you, there’s a marked difference between people who know what they’re doing and people who don’t know what they’re doing when it comes to sexual encounters.
This is one of the reasons I have come to prefer hooking up with other sex workers; they tend to know what they’re doing and have gotten over the kind of timidness that your average civilian experiences when it comes to having sex. I’ve almost completely overcome my own sense of sexual shame, no matter how ardently our anti-sex, anti-pleasure culture has tried to indoctrinate me otherwise. I wear the word “slut” like a badge of honor, because I like to have sex, I’m good at it, and there’s nothing wrong with that. I know that even now there will be people who read this post who will feel insulted or vaguely uncomfortable with its content, and that’s okay. We’re all on a journey when it comes to unlearning shame and the ways we’ve been taught to fear sex, and for some of us that process takes a lifetime. But I’ve gotten to a place where the power imbalance feels too great when I’m having sex with someone who is just at the beginning of that journey, because I’m simply much further along. In the same way that it’s wrong for an older professor to date their TAs, I possess a greater amount of accumulated wisdom and life experience regarding sex, and I’m at a place where I need this to be matched in my non-professional sex life.
When you’re a sex educator or erotic professional, unfortunately you often default to being the “expert in the room” in your own personal sex life. Many sex educators and sex workers I’ve talked with about this phenomenon feel like they’re always on the clock between the sheets (with the notable exception of other sex geeks who have taken the time to work on being good lays; you’re the real ones). I’ve taught countless partners and hookups about good consent practices, how to use various forms of safer sex methods, and better sex techniques so that they can go on to have more fulfilling sex with their other partners in the future. (To all the people who have fucked my exes after me, you’re welcome!)
This isn’t a flex and it isn’t a brag. It’s actually a sound condemnation for how piss poor America’s education system is when it comes to human sexuality. People want to have good sex, (duh) but they’ve been burdened by shame and feelings of inadequacy and don’t know where to turn to get better at having sex. There’s no shortage of terrible advice out there (the lad mags and Cosmo articles of yesteryear did a whole generation of us dirty) and anyone with a front-facing camera on their phone can start a TikTok account and call themselves a “sexpert,” no matter their lack of training or ability to fact-check before they repeat misinformation.
After many years of essentially teaching for free, I decided to start my own Intimacy Coaching practice. I believe hands-on learning is vital when it comes to good sex. There’s only so much you can read in a book or blog post (hi) because sex is an embodied practice, not a cerebral exercise. This is part of the problem, too — we Westerners have bought into the mind/body split, and we ruminate and make an intellectual mess of our sex lives. We get disconnected from our sense of pleasure because we don’t know how to read our own bodily cues. Many of us have ignored our erotic bodies for so long that we have no idea how to engage. Many of us can’t even tell when we’re hungry because we have shut down the lines of communication between mind and body. But like like intuitive eating, we can learn to tap into the intuitive erotic.
How to Have Sex with Basically Anyone
For the sake of a better sex life for everyone out there reading this, I’m here to share some of the tried and true tips for having sex with absolutely anyone, irrespective of their gender or genital anatomy. This is enough to get anyone started, even if you’ve never had sex with another person before! It’s a bold claim, yes, but I intend to back it up.
A quick disclaimer: Despite the admittedly provocative title, this is not a pick up artist type of post. This is not about how to “get chicks” or trick someone into fucking you or anything like that. This is more about what to do when you’ve gotten to the point of someone genuinely liking you enough to want to have sex with you. That first bit is up to you.
Pre-Work
Do Some Basic Brushing Up on Anatomy. I’d personally recommend doing this for the anatomy of people with vulvas and people with penises, irrespective of what your own sex life or desires look like. Learning more about the anatomy of people with intersex conditions/differences of sexual development is also beneficial to everyone. Why? We have far more in common than different when it comes to nerve endings, erogenous zones, erection, lubrication, etc. It’s like being able to switch between using a Mac or Windows machine. Seeing commonality and appreciating variation or difference leads to greater overall understanding. Why This Works: Did you get amazing sexual anatomy lessons in your high school sex ed? [Waits for the laughter to stop] Me neither. I had to supplement a lot of my knowledge with independent research. And it’s really paid off! I understand more about how the human body works, and my clients, hookups, and partners benefit from me knowing where things are, how they function, what feels good, etc. It’s also led to better self-knowledge in my solo sex practices, but we’ll get to that point in a moment. Some sources I like: Teen Vogue on the Penis, Teen Vogue on the Vulva/Vagina and the images below from Vielma.at
Pet A Friendly Animal. Cats and dogs are really good at telling us what they like and don’t like without using their words. You can tell right away if an animal likes the way you’re petting it. They’ll purr, sigh contentedly, close their eyes, bump their head into your hand, roll over and show you their belly for pets, etc. Because non-human animals don’t have shame associated with pleasure, you can learn to “read” their bodies easily. This is also much lower stakes than with a new date. A cat or dog will just roll over or walk away if they don’t like what you’re doing. Much of touching for pleasure is non-sexual, but getting good at non-sexual touch will help lead to better sexual touch. Why This Works: I’m good at reading human bodies in part because I’ve always had pets and I’ve had lots of practice touching other beings. Learning to read bodily cues is imperative for a good sex life. Consent is both verbal and non-verbal. Human beings also give non-verbal embodied clues as to what we like: we smile, moan, our breathing quickens or slows, our eyes close so we can focus on stimulation, our muscles tense or relax, etc. We also express ambivalence and displeasure: We wince, go blank, move away, etc. Each individual is different, so you have to learn to “read” their body differently. Understanding non-verbal cues means you can adapt more readily in the moment when you’re having sex with someone.
Look At Your Body in the Mirror. This might sound scary as hell, but follow me on this one! This is part of an exercise surrogate partner therapists will do with their clients before moving on to sexual activity. Looking at your whole body, in the nude, in front of a full length mirror will help you evaluate and appreciate all of it. Why This Works: Everyone has hang-ups about their body. Everyone. I’ve watched the most drop-dead gorgeous strippers who made thousands of dollars a night pick apart their stretch marks in the dressing room. But facing, rather than hiding from, the parts of your body that aren’t your favorite can help you have a more balanced sense of what your vessel has to offer. The more we avoid seeing something, the bigger and worse it can feel in our minds. The more exposure we have to it, the less loaded it becomes. We can move from, “My cellulite is fucking disgusting,” to the less harsh “Ugh, there’s my cellulite again,” to the more neutral “Yep, I have cellulite” over the course of time. There’s another benefit here: If we can learn to see our bodies the way our lovers see them, we can learn to find ourselves more attractive. I’m not personally my type, but when I look at myself in the mirror, I make a concerted effort to imagine what the people who are attracted to me see. I have certain body parts I’ve learned to really love, and some I merely tolerate. My sense of body neutrality has led to body confidence. I’ve also had the benefit of seeing hundreds of people naked, up close and personal, and I have a much more realistic sense of how my body fits into the broad scheme of what it means to be in a human body. My body is just as good as everyone else’s. No more, no less. Self-loathing or fears of inadequacy can tank our sex lives. Being able to develop a sense of body neutrality (even if we can’t get to body positivity or body confidence) can help us show up and be more present during sex. It’s tough to focus on our own or our partner’s pleasure when we’re preoccupied with whether' we’re ugly, or if our dick is too small, or our tits are too saggy, etc.
Develop a Self-Pleasure Practice. This is huge! Figure out what kinds of sensations you like and don’t like. Knowing yourself first is a major step on the way to being a better lover with another person. Why This Works: Being able to say to a partner, “I like light touch on my thighs but not on my back,” or “I really only get off from penetrative sex,” or “I like a loose grip and lots of lube when you stroke my cock” is really, really helpful! There are some basics that remain true across bodies and experiences, but each human being is their own little snowflake, with unique preferences and desires. Being able to communicate your own to others will lead to a better sexual experience for everyone involved; you won’t have to suffer through sensation you don’t like, and they won’t have to guess and grope their way through the encounter.
During Sexual Encounters
State What You Want, Then Ask For It. This one is a universal go-to for me! Examples include: “I’d really like to kiss you. Can I kiss you?” or “I want to hold you down by your throat and fuck you senseless. Would you like that?” Why This Works: It’s simple. I’m telling you what I want so you don’t have to guess. Then I ask if I can do it. Both parts are vital here. You can’t just tell someone you want to do something and then do it without getting their consent. And just asking for something without stating you want it doesn’t set an intention and doesn’t plant a seed of desire. It can feel mechanical. Yes, it can feel vulnerable to name your desire, but sex is vulnerable. Even casual encounters involve some level of vulnerability. And this doesn’t only apply to topping/acts of dominance: “I want you to tie me up and humiliate me tonight. Will you do that?” Believe it or not, submissives/bottoms can and should ask for what they want! I love a vocal sub or bottom. Not bossy, but self-possessed and aware of their own likes and dislikes. A Note for the Shy: If I’m feeling shy but I want to approach someone at a party, I’ve used the line, “Hi, I’m feeling kinda shy but you’re really cute. What’s your dance card like tonight? Can we find time to connect/make out/[whatever]?” It works like a charm!
Ask Where Someone Doesn’t Like to Be Touched. I start every new encounter with someone like this, whether they’re a first date or a new client. Here are ways I phrase this: “Have you had any surgeries or injuries that make certain parts feel painful or uncomfortable to touch? Do you have neuropathy? Have you had a traumatic experience involving a certain body part or sex act that you’d like to have off the table?” Why This Works: Sex is about trust. Whether it’s a one night stand, a paid gig, or because you’re celebrating your Golden Anniversary, trust is vital for good sex. I want to show the other person that I care about their body and I don’t want to accidentally do something that will hurt them or take them out of the experience. Asking about where they don’t want to be touched and then demonstrating I was paying attention by not doing it is a huge trust builder!
Don’t Just Lie There. I had sex with someone recently who didn’t try to touch me at all. I asked them what they wanted, if my touch was working for them, if I should adjust, etc. and they gave me little workable feedback. I felt like I was the concierge of the experience and they just kind of stayed still. Sex is collaborative, and this didn’t feel collaborative. I wasn’t sure if they were into it and that felt bad to me. I wanted them to enjoy the experience as much as I did. I liked them a lot but after that date we didn’t hook up again. If they had been a bit more active, told me what they wanted, or tried to touch me at all, I would have absolutely given them another shot. Why This Works: Being an active participant during sex communicates genuine interest and enthusiasm. For people socialized female, this might be a tough one. Many of us have been socialized to let sex happen to us, and may not even know how to take an active role in sex or speak up when asked a direct question. But assuming someone will take 100% responsibility for making the entire encounter happen doesn’t set anyone up for success. If you’re a pillow prince/ss hooking up with a stone top that could work out splendidly, but that kind of thing needs to be negotiated ahead of time. A quick note: I’m not talking about tonic immobility or dissociation. That is our body’s way of protecting us during a violent sexual encounter. If you’ve ever felt like you couldn’t move during sex, or like you were watching it happen from across the room, that is more likely related to trauma and I’m absolutely not blaming anyone for that. If you can get help, talking through such experiences with a trusted therapist or working with a trauma-informed intimacy coach can help you overcome that fight/flight/freeze reaction during sex.
Check In Afterward. One of my dates impressed the living fuck out of me once. We met at a sex party and he later reached out to me when he was passing through my town to ask if we could hook up. We had a date and the next day he followed up to say he enjoyed the experience, asked me what I liked and didn’t, asked if I’d like to do it again sometime, and left it really open ended and assured me we’d stay friends if I didn’t want to. Dear Reader, it was the hottest fucking thing that had ever happened to me up to that point in my life! We’re still in contact to this day and in fact I went to his wedding last year. (It was a wedding between two bisexual, polyamorous folks and he invited me to make out with him after the ceremony. I live a charmed life.) Why This Works: I’ve used his template ever since, and it communicates genuine care for my dates and clients. I want them to know that I’m invested in their good time. I want them to know I will still think well of them and won’t get butthurt or lead with a bruised ego if they have critical feedback for me or don’t want to hook up or hire me again. I can take what they have to say either way. I can’t think of a more desirable quality in a sex partner!
Bonus: What About “No?”
Be Gracious About Hearing No. “No” is a gift. “No” means you can reserve your energy by not pursuing something not meant for you and focus your attention elsewhere. Learning to graciously accept a “no” is a life skill not many of us are taught, and for those who are socialized to do the majority of pursuing (e.g. those socialized male, those who are more butch-presenting) learning to get good at getting turned down is so important. Why This Works: Getting upset and weird with someone who has said no to you is a huge mark of emotional immaturity. It’s a major turn-off. Under no circumstances should you ever insult or abuse someone who has simply told you they’re not into you. If you’re interested in getting into kink scenes or group sex, swinger, or other alt-sex communities, other people will be watching you to see how you handle a “no.” If you throw a tantrum or storm off, no one else will want to come within a mile of you. My favorite go-to line if someone turns me down (yes, it happens a lot!) is to say, “Okay, thank you! Have a good night,” and then move on. Just because I have a lot of sex doesn’t mean everyone wants to have sex with me. I’m not for everyone, and I’m also not attracted to everyone. The world is huge and there’s plenty of fish in the sea. I still feel intimidated about approaching people sometimes, but by getting rejected a lot, I’ve learned that I can withstand it and be okay on the other side. It won’t kill me to hear a “no,” and in fact it only gets me closer to another “yes” waiting around the corner.
Use the No/And Method. If you’ve ever done improv or know anything about it, you know one of the core skills is to “yes/and” someone’s suggestion. If you’re setting the scene at the DMV, your improv partner is supposed to go along with it and pretend you’re both at the DMV. If they say, “No, we’re not at the DMV,” the scene stops there. Conventional wisdom states that this makes for bad improv. However, in our sex lives, sometimes we need the scene to stop there. “No” can be a complete and valid sentence (see above). But what if we do want to have sex or connect, but just not by doing that particular thing your partner suggested? They really want to do X, but you’re just not feeling it. You got bad news at work. The sociopolitical climate has zapped your erotic energy. For whatever reason, you’re not up for it. Here’s where No/And comes in. Why This Works: “No, I’m not up for getting fucked, but I’m happy to give you head,” or “No, I’m too tired for sex, but I’d love a massage,” or “No, I don’t feel like dressing up like Superman and chasing you around while you sniff my dirty socks and oink like a pig, but you can still sniff my socks while we watch TV.” It’s about finding some kind of common ground. If you’re up for connection of some kind, but without some of the bells and whistles, No/And is a helpful framework. Giving an alternative is more helpful than just saying “no” and leaving it at that. It’s kind of like when someone is hungry and turns down every restaurant you suggest without making a suggestion of their own. Having an alternate option can be immensely helpful and lets your date/partner know you still want to connect but aren’t up for the specific thing they mentioned.
So there you have it, a handy list of things I’ve learned and applied in both my personal and professional sex life. I hope you feel inspired to practice this yourself; you hereby have my blessing to go forth and fuck like a pro!
I hope this has been helpful for you. If any of this has been thought provoking but you’re wanting a bit more, or want to dig deeper with some one-on-one coaching, I’d love to hear from you! Feel free to find me at JulesIntimacyCoach.com where I’m available for hire as an educator, consultant, and hands-on coach.