How to Prepare for First-Time Sex

6 Things to Know (& 6 Things to Own) Before You Have Sex for the First Time

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Gearing up to — as they say — lose your virginity can be a stressful time.

And while experts caution that thinking of sex in these terms, with things like “popping cherries,” “losing your V-card” and “becoming a man” is misleading, counterproductive and even harmful, it’s a strange thing to be on the other side of the fence, wondering when your turn is going to come.

You might feel like all your peers are having their first sexual experiences before you, or that the sexual activities you’ve engaged in “don’t count” as real sex. Or maybe you just really want to impress someone you care about by being “good in bed” — or at least not terrible.

Even if they may be somewhat overblown anxieties, all of these are completely understandable (and common) concerns for people who’ve yet to experience first-time sex.

Luckily for you, AskMen spoke to a handful of sex experts to help you get the information you need, both when it comes to what to know and what to own before you have sex for the first time.

What to Know Before Having First-Time Sex

There’s No One Right Way to Have Sex

“All forms of sex — oral, hand-sex, etc. — all count as sex,” says SKYN’s sex and intimacy expert and author Gigi Engle. “We put so much pressure on intercourse and this can really pressure us to perform, which isn’t great for anyone. Instead of framing intercourse as the only kind of ‘real sex,’ consider all sex ‘real sex’ it makes everything a lot more pleasurable.”

Furthermore, Engle points out, “Eighty percent of people with vaginas don’t orgasm from vaginal penetration, so that is something to keep in mind during sex.

If you’re sleeping with a cis woman or trans person with a vagina, then, “Your partner is more likely to orgasm through oral sex, hand sex, and sex with toys,” she explains. “It doesn’t mean intercourse isn’t great and fun, it just means it should certainly not be the only thing on the table.”

From that perspective, there’s absolutely nothing wrong with experimenting with oral, fingering, handjobs, dry-humping and other forms of non-penetrative sex to start off with. If you’re not comfortable trying penetration, don’t feel pressured to jump into it.

It’s OK to Go Slowly

“Be sure that you’re breathing deeply and not rushing into penetration,” says Engle. “You want to be fully aroused and your partner to be fully aroused before trying penetration.”

“For people with vaginas, it can be really helpful if they have an orgasm before they attempt penetration,” she says. “You can do this with oral sex or a toy. First-time sex should not hurt and if anything does, you should stop and take a beat before trying again, being sure to communicate thoroughly as you move through the process.”

Regardless of your genitalia, Engle notes, it’s important to remember that “first-time sex is not something to ‘get through’ or ‘endure’ — it should be pleasurable and enjoyable.”

Porn Is Not How Sex Should Look

“Porn sex is performative,” says Jess O’Reilly, Ph.D., sexologist and host of the Sex With Dr. Jess Podcast. “It can be hot, exciting, inspiring and titillating, but it’s often not a depiction of what sex looks, feels and sounds like once the cameras are off.”

As well, O’Reilly notes, “The way you show and express pleasure may also be different than what you see in porn.”

“Because porn is primarily a visual (and audial) medium, some sexual responses may look and sound more exaggerated than how you and a partner respond in real life,” she explains. “Not all orgasms are loud and earth-shattering. Not all bodies move in the way they do in porn (because they’re moving for the camera — not only for pleasure). Not all bodies look like they do in porn. Not all erections are long-lasting and rock-hard. Not all women want you to ejaculate on their bodies/faces. It’s OK to be into the things you see on porn, but don’t expect that everyone else is too.”

Communication Is Essential

Speaking of porn, it’s also not a great model for what sexual communication looks like. Not because it doesn’t happen between porn performers, but because it happens off-camera and doesn’t appear in the videos you watch:

“Talking about the type of sex you’ll be having, sharing desires and fantasies, delineating limits and boundaries, safer sex practices (including testing), warming up before penetration, applying lube and condoms and getting to know one another are all a part of porn sex and non-porn sex, but they happen behind the scenes in porn,” says O’Reilly. “So don’t assume you can have sex without doing these things first.”

As well as talking about sex with your prospective partner(s) beforehand, talking about sex during the sex you’re having is also a good thing to get used to.

“Sex for the first time can be fraught with many concerns, fears, or pressure,” says Dr. Kate Balestrieri, a licensed psychologist, certified sex therapist and founder of Modern Intimacy. “Getting ongoing and enthusiastic consent is a sexy practice, and helps everyone feel confident that their health, safety, and pleasure are prioritized, which can allow them to relax more and have better sex!”

“Of course, desires and boundaries can change over time, so check in with a partner during sex to see how they’re feeling/what they’re into,” O’Reilly suggests. “A simple ‘do you like it like this?’ or ‘More here or there?’ can be a good place to start.”

Get to Know Your Own Body First

Whatever kind of sex you’re expecting to have, knowing what you like, how different sensations make you feel and what you are and aren’t comfortable with can go a long way towards making your first time a more pleasant one. If you’re going to be a penetrating partner, this can mean getting comfortable with masturbation, in one or more ways, but if you’re going to try being a receptive partner — whether the other person is penetrating you — you’ll want to familiarize yourself with how your anus works.

“For receptive anal sex, set aside time beforehand to get to know how your equipment works and what everything feels like down there,” says Lawrence Johnson, cofounder and CEO of Pure for Men, a wellness brand founded by and designed for gay men starting with a best-selling proprietary fiber supplement. “Experiment with lubrication, a sanitized set of fingers and/or toys to calibrate your brain with the variety of sensations that you’ll feel during anal sex.”

“You might be surprised to learn that what normally feels like a bowel movement has a completely different application in the context of receptive anal sex,” Johnson adds. “A little solo practice in the days leading up to ‘game time’ can also help avoid any pain as you start to work your way up to the real thing, size-wise.”

Quality Sex Products Are Your Friend

If you’ve never had sex before, it’s only natural that you might not own any sex products. But if you’re old enough to buy them yourself, and you have the money, spending a little on some quality products is a good move — and getting a trusted friend or even family member to hook you up with some if you’re not old enough can also work.

Of course, it’s often possible to get condoms for free, as many organizations give them out to promote safer sex, but condoms aren’t the only things to have on hand. If you’re planning to engage in penetrative sex, and especially if you’re going to have anal sex, a sexual lubricant is a must.

“Lube is your best friend!” says Fabian Prado, cofounder and CMO of Pure for Men. The anus “is not self-lubricating like the vagina, so you want to make sure you have a good lubricant.”

As well as condoms and lube, some other products can definitely benefit you for your first time. Of course, there’s no one right product for anyone, and even high-quality, well-rated products will be the wrong fit for many. Still, it doesn’t hurt to check out some respected brands’ offerings:

Products to Own Before Having Sex for the First Time

Note: While many of the below products are recommended by experts with ties to the brands they’re suggesting, AskMen stands by the recommendations from an editorial standpoint, as these are all brands and products we have tested before.

One Condoms

Best for: Finding the right fit

With condoms, fit is a huge part of the experience. A too-big condom can slide off mid-coitus, exposing you both to the potential for things like sexually transmitted infections and unplanned pregnancies.

However, a too-small condom won’t provide adequate coverage, and it could also come off, as well as simply feeling awkward. While you could buy lots of different brands and try them on to see what works best, there is a way to get a custom fit — One condoms.

“I like One condoms because they come in so many different sizes,” says O’Reilly. “They have measuring devices you can print off to find the perfect fit.”

$15.00 at MyOneCondoms.com

Astroglide Organix Lube

Best for: Lubricating vaginal penetration

“Lube makes sex hotter. Just a few drops can increase the ways in which you can play — from techniques to positions and beyond. If you’re having sex with a vagina, consider a water-based lube” like this one, says O’Reilly.

$14.00 at Walmart.com

Pure for Men Coconut Lube

Best for: Lubricating anal sex

Water-based lube may be great for vaginal sex, but it’s less ideal when it comes to anal penetration. If you’re gearing up for first-time anal sex, you’ll likely want a longer-lasting lube so there’s no danger of it drying up during the act.

For many people, the go-to here is a silicone lube, but not in all cases.

“I used to be a silicone lube guy, but hated the oily mess it can leave behind on sheets, walls, headboards and ceilings,” says Johnson. “I made the switch to our Coconut Lube a year ago and have never looked back. It smells and tastes great while offering the smoothness of silicone coupled with the ease-of-cleaning you get with water-based.”

$11.99 at PureForMen.com

Trojan Extended Pleasure Delay Spray

Best for: People worried about finishing too quickly

“A common concern for those new to penetrative sex is whether they will last as long as they want,” says Balestrieri. “Orgasm control is a skill, and one that can be developed over time.”

“While there are exercises to help with orgasm control, if you’re concerned about early ejaculation,” she says. Using a delay spray, like this one from Trojan, Balestrieri says, “can be a bridge to help you delay orgasm until you learn how to do it somatically.”

$12.98 at Walmart.com

SKYN Tremble Massager

Best for: Experimenting with a sex toy

Sex toys can be a huge part of your sex life. And while there’s no pressure to get into them right from the get-go, there’s also no harm in learning to get comfortable with them early. Particularly if you’re going to have sex with someone who’s been using them already for solo play, trying out a simple toy like the SKYN Tremble can be a great approach.

“This toy is perfect for beginners,” says Engle. “It’s small, yet powerful. It can be used during intercourse to provide some much needed clitoral stimulation for first-timers, making it more likely a person with a clitoris will have an orgasm during penetration.”

$24.99 at Amazon.com

Durex Real Feel Condoms

Best for: Those with latex allergies or sensitivities

The majority of condoms out there are made of latex, which is a very useful material, but it does cause issues for people with allergies or sensitivities to latex. If that’s you — or if that’s your partner — you’ll want non-latex condoms, like Durex’s Real Feel ones.

$19.99 at Amazon.com

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Source: AskMen