First Time Sex 101: How to Lose Your Virginity

Nervous for Your First Time? Here’s What You Need to Know to Make It Memorable

Being a virgin, especially later in life, can be stressful. You’re constantly pressured by friends and the culture at large to do the deed, to lose your virginity as soon as possible, often without care or concern about who you’d lose it with. If you’re a boy or a man, you may even be singled out as weak, unmanly or less than, all because you haven’t met the right person.

Guys who’ve already had sex, meanwhile, can strut about confidently, knowing they’re handsome, masculine and sexually irresistible. Whatever truth there is to that perception, it’s not as black and white as those situations would suggest. Being sexually inexperienced, even when you want nothing more than to lose your virginity, doesn’t need to be such an anxiety-ridden time of your life.

In order to help debunk some of the harmful and confusing myths around the subject, we spoke to a variety of sex experts, psychologists and regular people about what losing your virginity means, and how to go about getting it done the right way.

What Does “Losing Your Virginity” Mean?

The concept of losing your virginity is not as simple as many people make it out to be. Traditionally, losing your virginity has meant engaging in penetrative sexual intercourse, whether penis-in-vagina or penis-in-anus.

However, not everyone sees it as that. Some would argue that receiving (or giving) oral sex would count; between a straight couple, some would argue that anal sex doesn’t even count. Then there’s the questions of how long it lasts, whether anyone enjoys themselves (or climaxes), and whether it was consensual for both parties.

“I can’t say what counts for everyone,” says Jess O’Reilly, Ph.D., host of the “@SexWithDrJess” podcast. “Many of the young straight, cis guys I work with often consider themselves virgins until they put their penis in a vagina. But there is great variation and it seems young folks are more open to seeing sex as an experience that can involve a range of acts — not simply a singular one.”

According to Kayla Lords, writer and sexpert for JackandJillAdult.com, widening “our definition of sex to include anything that offers sexual pleasure” means the loss of virginity would be less clear cut, dependent more on the person’s mindset than the act itself.

“Oral sex is sex (no matter what you may have heard),” she says. “Fingering a partner is sex. So are hand jobs. Mutual masturbation (masturbating together or masturbating each other) can be considered sex. Once you realize how big of an idea sex is, whether you’re a virgin or not becomes harder to define. You could easily say that the first time you masturbated (sex with yourself), you were no longer a virgin — and that would be correct for you. Why? Because virginity isn’t a thing you have or lose… it’s a cultural idea, and it can mean anything you want it to mean.”

That means the old idea of the sexual “bases” where first base, second base and third base are understood to be increasing levels of sexual intimacy (often defined as French kissing, manual stimulation and oral sex before arriving at penetration) is outmoded, and possibly harmful, too.

“The idea of bases and getting to them is extremely limiting,” says Lords. “Is there really an ‘order’ to becoming sexually active with a partner? Does touching a partner’s nipples before you touch their clit really mean you’ve advanced a level? I don’t think so. Becoming sexually active and intimate with your partner isn’t a game to play in the sense that you can get so far but say you haven’t ‘done anything.’ If you’re providing or feeling sexual pleasure, then it doesn’t matter what ‘base’ you’re on.”

What’s the Average Age to Lose Your Virginity?

Lots of guys worry that they’re “behind” when it comes to losing their virginity, fearing that they need to lose it sooner rather than later. As a result, they focus on what other guys are doing — potentially to their own detriment.

“Many variables play a role in identifying average age of first sexual encounter, including the fact that we all define sex differently,” says O’Reilly. “Some count oral, others count anal and others count vaginal penetration as sex, and research confirms that there is no universal definition.”

“The first time I had sex I was 18 years old. I think it lasted all of maybe 15 seconds. We tried again half an hour later and that time lasted maybe a minute or so. Definitely none of the penetrative sex I had for the first 10 or 15 times was any good for my partners. But I started learning how to do cunnilingus, so that helped.” – Ian, 30

“If we look at reports of penis-in-vagina sex, the average age is 17,” she adds. “We have to be very mindful, however, that there are some considerable limitations related to self-report data when it comes to sex. A recent study found that more people are opting to delay or abstain from sex into their twenties.”

However, the concept of “average” and “normal” are very different things. You can lose your virginity much younger or older than average without there being anything wrong with that, or with you.

“There is no ‘normal’ age for a guy to lose his virginity,” says Lords. “Instead of focusing on a specific age, guys should think about whether they’re ready for sex or not. If you’re not comfortable having a conversation about STIs, pregnancy and contraception, you’re probably not ready for sex yet.”

How Important Is Losing Your Virginity?

“Lost my virginity at 26 to a friends-with-benefits situation. Low-key, no drama, 10/10 would recommend.” – Robin, 31

With all the stress many guys feel about losing their virginity, it can be hard to know just how important it is to do the deed.

If you’re still a virgin in your late teens, every waking moment might be filled with anxiety as you try to figure out how to swipe your V-card as soon as possible. On the flip side, you might be a 50-something-year-old virgin, content to die of old age never having had sex. How badly you want to lose it is a personal thing, but in purely objective terms, it’s kind of a made-up concept. Basically, you shouldn’t care about it too much.

“Virginity is a social construct that people decided was important hundreds of years ago. So whether it’s important to lose your virginity or not is actually up to you,” says Lords. “There’s nothing to ‘lose’ when you say ‘losing your virginity.’ There is only experiencing sex or not experiencing sex.”

Here’s one thing worth remembering: If you’ve been feeling pressured by your peers to lose it, that’s often based on outdated ideas of masculinity that you shouldn’t feel the need to bend to.

“Traditionally, […] virginity has been seen in the media and in life practices as something girls should wait to lose, and young guys should lose it as soon as possible,” says Mackenzie Riel of adult novelty and romance retailer TooTimid.com. “[But] it should be a personal decision whether or not a person wants to lose it. There is so much pressure that comes from society to one way or another, your situation will never be exactly like somebody else’s, anyway.”

Jor-El Caraballo, a relationship therapist and co-creator of Viva Wellness, also points out that the whole concept of virginity should be held in your hands, exclusively.

“The importance of ‘virginity’ is healthiest when best controlled by its holder,” he says.“Each person must decide how important virginity, and therefore sex, is to their lives. Taking in and exploring all of our messages from religion, family, school, etc. and asking ourselves tough questions about sex and desire is the healthiest thing we can do. And if you feel stuck, you can always consult with a therapist who works closely on sex- or sexuality-related issues for non-judgmental exploration of all these things.”

O’Reilly agrees that virginity (and the concept of purity associated with it) can be really confusing and a very narrow way of looking at a person.

“Virginity is a social construct,” she notes. “There was a time when we believed that being a virgin referred to not having put a penis inside of the vagina (which would suggest that tampons, fingers, sex toys, tongues, etc. wouldn’t qualify), but not everyone plans on putting a penis inside of a vagina, and even those who have done so (or plan to do so one day) classify other sexual activities as sex. If you’re a lesbian who has been having sex with your partner for 10 years, are you still a virgin?”

At the end of the day, losing your virginity really means having sex for the first time — and what that means, exactly, depends on what you’re into, whether that’s penetrating someone or being penetrated or both; whether it’s oral, or anal, or vaginal sex, or even something else.

What Should You Know Before You Lose Your Virginity?

The prospect of waiting to have sex for the first time might feel excruciating, but that doesn’t mean it’s something you should just casually rush into.

“I wish I hadn’t had sex until I had a career. Sex itself is overrated and took up so many stupid hours of my young life. For the record, I think [losing your virginity] is special, but non-procreative/recreational sex is not special, and is rather a distraction.” – Mary, 28

If you’re planning on having sex for the first time, there are a few basics you should take into account before stripping your clothes off.

Get Comfortable Talking About Sex

Just because you can talk about sexual topics doesn’t necessarily mean you’re ready to actually have sex. If you can’t be honest and serious about it in conversation, that might be a sign that you should wait.

“The conversation I have with young men (including my own teenage son) is this,” says Lords. “If you’re not willing to talk about sex with your partner, use proper terminology for the sex acts and body parts involved, gain full, enthusiastic, and informed consent from your partner, and discuss condoms and contraception, you’re not ready for sex with a partner.”

“But,” she adds, “you can have sex with yourself any time you want.”

Don’t Set High Expectations

It can be easy to get carried away thinking that sex is the best thing of all time and your first time will be amazing. Unfortunately, that’s probably not going to be the case.

“It doesn’t have to be mind-blowing and it likely won’t be because it’s your first time with a partner,” says O’Reilly. “The first time you tried anything (e.g. threw a baseball or cooked a meal), you probably weren’t as good as you are now. Enjoy the process and don’t get hung up on timing yourself or ‘spectator-in’, which refers to watching the experience unfold like an outsider instead of living in the moment.”

Don’t Feel the Need to Hide Your Inexperience

If you feel embarrassed by your sexual inexperience, it might be tempting to lie about it or simply not tell your partner — but that might not be the best strategy, according to O’Reilly.

“You can let your partner know that it’s your first time if you’d like,” she says. “You don’t have to, but it can be helpful. Let them know what you have tried and what you enjoyed. And consider letting them know what’s new to you and how they can make the experience more comfortable and pleasurable. If ‘being a virgin’ is an issue for them (it won’t be for most people), they might not be a good fit for you.”

Don’t Do It Unless You Feel Ready

Most importantly, don’t let anyone (yourself included) pressure you into it. If you don’t feel ready, then you aren’t ready, and it’s OK to say that or to stop things before they go too far even if that’s right as you’re about to do it.

“You should feel prepared and safe,” says O’Reilly. “Much of the information on sex and virginity focuses on supporting young women, but being physically, emotionally and practically prepared and supported is essential regardless of gender.”

So what does feeling prepared include?

“Being prepared might include talking about your desire with your partner; sharing concerns and uncertainties openly; discussing and planning for safer sex — not just condoms and lube, but also your own needs and boundaries (you can talk face to face or start planning via text); taking some time to consider why you want to have sex,” she adds. “What’s in it for you? Do you want to the pleasure, the connection, the exploration, or some other perceived benefit? If you’re motivated by cultural pressure, perhaps reconsider. Your ability to have sex will always be there, so you don’t have to do it right now.”

First Time Sex Tips

So the moment has finally arrived. Maybe it’s with a partner, maybe it’s with a friend or maybe it’s with someone you just met. You know more or less what you’re in for, you feel comfortable with yourself and the concept of sex, and you feel ready. But what should you actually do before the sex takes place?

Practice Safer Sex

As unprotected sex can cause pregnancy and can allow for the transmission of sexually transmitted infections (STIs), you should absolutely use a condom when having sex, especially if it’s your first time.

“Do use a condom!” says Riel. “That’s a given anyway, but even if it seems safe enough not to, you’re better off wrapping it before tapping it.”

“I was 19 — three months into a relationship. We’re fooling around and she tries putting a condom on. She’s furiously trying to shove it on and it’s not going well, so I lose interest. We’re perplexed. These things stretch! It should be fine! Turns out I needed to buy the Magnum ones. So the next week, we go out and do that. We repeat the same sort of activities. We try these new ones. They work! Magic. It still makes me laugh that I didn’t clue in and wondered if the original ones were defective.” – Robert, 34

If you don’t know how to properly use a condom, you should prioritize familiarizing yourself with how they work before having sex with anyone.

Talk About It

It might not seem sexy to kick off a bedroom session with a conversation about how you’re feeling, but not talking about it could lead to a potentially pleasureless experience. The more you communicate with your partner, sharing what each other wants and doesn’t want, the better your chances of having a positive experience.

“Talk to your partner and be very certain they’re into what you’re about to do,” says Lords. “Feeling awkward is normal. When in doubt, ask your partner what they want you to do. ‘Do you like this?’ and ‘Can I keep going?’ are always good options.”

Take Your Time

You might have waited a long time for this moment, but that’s all the more reason to draw it out and savor it — don’t try to rush things.

“Take the time to explore each other’s bodies,” says Lords. “Sex isn’t just penetration (in some cases, it doesn’t involve penetration at all) so focus on touch, pleasure, and the experience.”

And if you orgasm really quickly? That’s normal — you probably will have trouble delaying your orgasm during penetration until you’ve gotten more practice. Lords says there’s an easy solution for that, Focus on your partner first.”

Try Different Positions

Depending on whether you’re an avid porn-watcher or not, you might not have any real understanding of what different sex positions look like — but that’s OK.

“You likely won’t find the right position off the bat,” says Riel. “You’ll have to move and adjust so you and your partner are both comfortable. Most people lose their virginity while doing the missionary position, but you may find that you need to find a different angle or try something different. If that freaks you out, just go with standard missionary and don’t experiment beyond what you’re comfortable with.”

Don’t Be Too Critical of Yourself

Men are also often expected to be talented lovers who make their partners orgasm every time. Given this is your first experience, you shouldn’t focus too much on your performance or what does or doesn’t happen. Instead, try to enjoy yourself and make sure your partner enjoys themselves, too. There’ll be plenty of time to work on everything in the future.

“Stop worrying about how ‘far’ you get or whether what you’re doing ‘counts’ as sex,” says Lords. “It’s all sex, and all that really matters is that you both have a good experience, no matter what that looks like.”

What Does Sex Feel Like?
The Best Positions for First-Time Sex
Things to Consider Before Sleeping With a Virgin

Source: AskMen