5 Crucial Tips for Making Someone’s First Time Memorable — in a Good Way
5 Crucial Tips for Making Someone’s First Time Memorable — in a Good Way
In recent years, sex experts have attempted to shift the way we think about virginity.
The old model — which prized sexual inexperience in women and disparaged it in men — has come to be seen as incredibly regressive, and a contributor to poor outcomes, pushing people to lie about their respective sexual experiences, and to judge others for theirs.
There’s also been recognition that penis-in-vagina sex is not the sole arbiter of whether someone has “had sex before” or not — nor should it be, considering many people never want or plan to engage in that particular kind of sex.
From this perspective, you can cherish the first time you engage in a particular sex act, without feeling like failing to do so means there’s anything wrong with you.
But while the new paradigm can help take the pressure off people who haven’t had sex, if you do see yourself as a virgin, it can feel incredibly frustrating to never have had sex before, regardless of how other people frame the issue.
The truth is, not everyone wants to have sex with a virgin. While for some, the thrill of being someone’s first time is potent, for many others, a virgin represents someone who doesn’t know what they’re doing, and who may experience pain, shame or discomfort when having sex, rather than simply pleasure and excitement.
But if the person you’re considering sleeping with tells you they’ve never had sex before, what should you know to ensure that you don’t make a mess of their first time? In order to find out, AskMen spoke to a number of sex experts. Here’s what they had to say:
How to Make Your Partner’s First Time a Good One
1. Don’t Rush Into It
While the other person — whether they’re your partner or someone you don’t know super well — may want to just get things over with, if you’ve decided to sleep with each other, it’s a good idea to take some time to establish ground rules and get on the same page about things first.
In short, you need to talk about things. That might not sound super sexy, but a lot of sexual trauma and pain has occurred throughout history because people were unwilling to have a conversation about matters beforehand.
Sex educator Kenneth Play, author of Beyond Satisfied: A Sex Hacker’s Guide to Endless Orgasms, Mind-Blowing Connection, and Lasting Confidence, recommends you “do most of the talking about sex while you have your clothes on! Have a conversation, then take a break (have a tasty meal, go for a walk, play a game, etc.), and then have sex later on!”
Separating the discussion from the act means you can both digest what the other person has said, ask follow-up questions, and that you won’t accidentally rush things in the heat of the moment.
2. Talk About Safer Sex
Part of the conversation needs to be about safer sex, according to Nora Langknecht, certified sex educator and marketing manager at FUN FACTORY.
“As the experienced one, you might need to take the lead on this,” she says. That means being up-front about things like testing status and STI prevention, as well as pregnancy prevention, and methods of choice for those things, such as condoms, birth control, PrEP, etc.
This doesn’t need to be a one-way conversation; a good idea is to “check in with [your partner] about what their sexual education has been like,” according to Play.
Another aspect of safer sex is making sure it’s emotionally safe, not just physically safe.
“Make sure to tell them that they can say no at any time,” says Play. “A lot of women will go along with whatever’s happening because it can be awkward to speak up, so you’ve really got to create an environment in which they feel safe to stop at any point, for any reason.”
This may be particularly true if the person you’re sleeping with has been socialized female, but people of any sex and gender can struggle to feel comfortable asking you to stop or change what you’re doing if they’re not having a good time in bed — especially if they’ve never done this before.
3. Ask Questions
If they have a vagina, ask the other person how they usually masturbate and whether they usually climax, Play suggests. That will give you useful information when it comes to what gets them excited and what their prior expectations of pleasure might be.
Another useful approach, regardless of what your partner has in their pants, is to ask questions while you’re having sex together as well. Play calls this “calibration.”
This doesn’t need to be a drawn-out interrogation that ruins the mood, but rather a simple check-in that allows you to get a sense of what you’re doing right or wrong.
“For example,” Play says, “asking ‘Higher or lower? Harder or softer? Faster or slower?’”
Paying attention to your partner’s responses, whether verbal or non-verbal, will give you a wealth of information about how to make them feel good, as well as how to avoid making them feel bad.
4. Focus on Non-Penetrative, Pleasurable Play Too
“Remember,” says Play: “first-time sex doesn’t have to be penis-in-vagina sex!”
(Or penis-in-anus sex, if you both have penises.)
First-time sex can be oral pleasure, it can be manual stimulation, it could be dirty talk and mutual masturbation — expanding your ideas of what that means, or just talking about what things can look like with the other person — can open up possibilities that you might not have considered for an exciting, pleasurable time.
If you are going through with penetrative sex, say SKYN Condoms’ sex and intimacy expert and author Gigi Engle, “Read up on oral sex techniques, learn about the clitoris, and actually do the legwork to ensure that you’re giving this person a good first-time experience.”
“It’s just good form to be an attentive lover,” she says.
It’s also a good idea to dispel the myth that first-time sex will be painful — in part by making sure your partner is well-lubricated beforehand.
“A lot of people assume that pain is part of a first sexual experience, and that’s just not a given,” says Langknecht. “Focus on warmup (“foreplay”), exploring what feels good, and building arousal — this will make any sex that follows more comfortable and fun for everyone.”
5. Engage in Some Form of Aftercare
Depending on whether you’re in a relationship or not, the question of how to act afterwards may be more or less obvious, but either way, you should remain conscious that the other person just experienced a significant life event and may need to process that in some form or other.
That could take the form of them wanting to be paid close attention to, or it could mean they want to be left alone, too. Either way, being attentive to their desires is a form of aftercare that will go a long way towards making this a positive memory rather than a negative one.
“Don’t be the guy who fucks her and leaves her devastated,” Play says. “Be the guy who checks in the next day. That’s how you become a lover women brag about to their friends. A pleasurable first experience of sex, negotiated with kindness, that prioritizes her well-being, will set her up for the rest of her life.”
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