Guide on how to lose your virginity

Will it hurt?

If your idea of losing your virginity is penetration then yes, it might hurt. But how much can vary, and there’s lots you can try to minimise the pain. Firstly: foreplay foreplay foreplay. Get to know each other’s bodies first through touching, kissing and licking. If you’re turned on, your vagina will release natural lubricant, making penetration easier and less painful. But the most important thing is to try to relax. If you tense up, your vaginal muscles will too, sometimes resulting in a burning, stinging or aching sensation. Remember you can stop at any time if you don’t feel comfortable.

How To:

Next time you are having a not boring conversation in person with someone, nonchalantly pull out your smartphone (as people do quite frequently nowadays). Launch the app and record the conversation, if you have the Evernote widget installed it literally takes about 3 seconds to open a voice note recording the conversation. Place your phone on the table between you and the other person. At first, you may feel a little weird since the other person won’t know the conversation is being recorded. I’m not a lawyer but I’m pretty sure that provided you aren’t using the recording for commercial purposes, this is legal.


If you’ve been on a few dates with a girl, kissed her and she likes you just suggest that for your next date you get a room together

At the end of a date that’s going well but has no chance of ending in sex, in-person suggest that the two of you get a cozy room together next time. She’ll almost always accept. If you do this over text this is less successful. If she rejects your offer and says uhm… it’s too early for us to spend the night together! That’s fine if she’s still willing to see you again you’re making progress. Just make the offer again in a week. If she seems staunchly opposed to it move on to another girl.

Then spend a little bit of money to get a room at a decent hotel or off AirBNB. Meet her like normal for dinner or a drink and then go back to your place.

This goes against the pickup artist dogma that you should never tell a girl your plans to sleep with her. Pick-up artists suggest that you invite a girl out for a drink and then just nonchalantly invite her back to your room to watch a movie or whatever but I’ve had pretty good luck with being a bit more direct. Often I’ve been in a situation where I had been on a date or two with a girl and was eager to see if she actually liked me enough to sleep with me or be my girlfriend so I’ll just suggest that we get dinner and a room together for a romantic evening. This is a step above casual sex and if you’re dating a relatively conservative girl she’ll appreciate your chivalry and likely accept. It gives her the chance to shave down there prior and wear something that makes her feel sexy. Also in this crazy #metoo era, it mitigates the chances that she’ll impulsively sleep with you, regret it and cause you a world of trouble. In my experience it also makes the first-time sexual encounter a whole lot more comfortable; you won’t be in a huge hurry to close the deal and you get to have morning sex when you wake up together.

15. It’s not true that your soul will be forever attached to the first person you have sex with

Fox / Via Sure, you might still look back on them fondly (or not so fondly) when you’re talking to your friends 20 years from now, but you’re not going to be forever attached to this person if you don’t want to be, says Herbenick. This myth might come from the fact that many people do feel some sort of a connection to the person they lost their virginity to, but that’s more of a social construct than a guarantee.


As Phil Collins famously droned: “I’ve been waiting for this moment for all my life”. And, boy, haven’t you. So, yes, there may be a slight issue in that you… lose your issue quicker than anticipated. If you shoot your shot before you’ve even taken aim, don’t be disheartened; it really does happen all the time. If your pride can take it, make a small joke of it – don’t flay yourself alive, though – and chill for a bit, before going back to foreplay and having another go. Perhaps it would help if you orgasm through foreplay instead and then try again later, assuming you have all the time in the world and not 20 minutes in the stationery cupboard. Some people say if you think of something deeply unsexy – the big roundabout at Hemel Hempstead, a chef’s fingernails, a home appliance – then you can delay ejaculation, but I’m not sure this is a risk worth taking unless you forever want to associate your first penetrative orgasm with, say, a fridge freezer.

6. Get some exercise

Fitness is obviously important. Getting even a little bit of exercise weekly makes you look and feel better. You’ll have to take an honest look in the mirror and see how you need to change your priorities around health and fitness. If we’re being frank, your looks probably have a lot to do with your virginity. The chronic virgins or incels that I’ve known consistently were a bit out of shape and aesthetically sloppy.

But you don’t need to look like Channing Tatum to lose your virginity. In fact, being a little chubby or even underweight and skinny is not going to stand in the way of losing your virginity. Girls sleep with guys who are chubby or skinny as a rake all the time. The important thing is that you make some progress and improve your fitness.

When you go to the gym enough to see your body start changing and feel your mood improve it has this undeniable effect of empowering the rest of your life. It might take 2 months, it might take a month, it might only take a week of exercise and you’ll start feeling like the world is yours!

As a rule, aim to do something about three times a week that gets you sweaty.

  • Cardio — Just 15 minutes of cardio increases Mitochondrial density and output. I find that just a little cardio improves my cognitive baseline, mood, and verbal intelligence for several hours.
  • Pumping iron — Probably the quickest way to change your body and your hormones is resistance exercise. Moving heavy stuff around. If it’s been a while since you lifted weights you should try to do a session or two with a personal trainer, if you can’t afford this ask the employees or the other guys at the gym for a few pointers on your form. This can save you from costly injuries that set you way back in your fitness. For at least the first few months of weight lifting don’t worry too much about any fancy supplements. Going to the gym consistently is way more important than supplements at this stage.
  • HIIT — High-intensity interval training can be an ideal time-saving exercise lifehack for staying healthy, vigorous, and lean. Dave Asprey, the godfather of Biohacking, describes why this is such a quintessential exercise lifehack…

HIIT workouts alternate between intense bursts of strenuous exercise and brief periods of active rest.

HIIT subjects your muscles and cardiovascular system to extreme stress and then allows them to recover during the “active rest” period. This active rest period keeps your heart rate elevated so that you can still reap the rewards of aerobic exercise. It’s the happy marriage of two schools of fitness thought, and it might be more effective than either resistance or aerobic exercise alone. In fact, studies have shown that HIIT is up to ten times more effective at increasing growth hormone than resistance training or endurance training.(pp. 194–195)

Bodyweight exercises — Often you may not have the time or access to a gym to exercise but you can always do some bodyweight exercises. Check out this playlist. Unfortunately, many of us spend years of our lives sitting in front of a computer, every 60–90 minutes try to remember to get up for a minute or two — a great time to do some bodyweight exercises! You may be surprised that this increases your baseline energy levels throughout the day.

27. Videoblog

Vlogging can be a real game-changer for your communication skills!

  • You don’t need to script your vlogs. Pick a subject that interests you or something that you know about and just speak extemporaneously about it for 5–10 minutes.
  • You could also record a video letter to a friend or family member saying whatever you might have to say to them.
  • You don’t need to get any fancy recording equipment. Just use your webcam or smartphone.
  • Importantly, watch and listen to your vlogs. Which at first may be a bit painful, a lot of us are naturally cringeworthy in front of a camera. Record, watch yourself, and re-record a couple of times. It doesn’t have to be perfect but you should see yourself improving.
  • You may notice yourself using a lot of filler words; Uhms and ahs — instead make an effort to just pause and think about what you’re going to say next. Pausing while you’re speaking makes you sound intelligent and thoughtful instead of nervous and indecisive.

You may be thinking…

I don’t really want to become a vlogger! There’s already a million Youtubers out there. I don’t really want to broadcast my opinions out to the entire world.

Well, you don’t have to. You can upload but leave your vlogs unpublished — maybe you’ll want to share them with someone eventually. Or you can record them and just save them on your hard drive.

18. There’s no right time to have sex

View this photo on Instagram How and when you decide to do it is no one’s business but your own. You’re not a slut if you choose to lose your virginity, and you’re not a prude if you decide to wait. What’s more important than an arbitrary timeline is doing it for the right reasons and in a context you feel comfortable with, where you are actively consenting. “That you yourself want to — not that you feel pressure from a partner or that all your friends are doing it,” says Mark. “When somebody has sex for the first time for those reasons, they are more likely to regret it.”

Put on protection

Before you engage in sexual intercourse make sure that you have put on some protection. Then, slowly start inserting your penis into your partner’s vagina to penetrate her. Be attentive to her cues and her remarks. It is also a big deal for her and she will be the same if not more nervous. Once both of you are comfortable, try rocking gently back and forward until you find a comfortable rhythm.


There can be a lot of sentimentality attached to losing your virginity. Should it be someone you love, a special person you’ve known for years? Or is it about getting it out of the way as soon as possible – a quick bang with another on a drunken night out? It depends how you feel about it. Just make sure whoever you’re doing it with knows you want to have sex and, crucially, feels the same way. No need to say it’s your first time if you don’t want to – although it may be obvious when you try to stick it in their ear or something – but unless you’ve chosen somebody quite noxious to do the deed with, they’re likely to be very understanding if you do. Nobody wants someone else’s first time to be a disaster or emotionally scarring. Apparently.

2. Virginity Contributes to Slut-Shaming

Virginity is constructed so that we judge women based on how and when they started having sex.

Losing your virginity at the wrong age (usually being “too young” in this case), at the wrong time (“too early” on in a relationship, or not during one at all), with the wrong person (usually someone you aren’t “in love” with) or with the wrong feelings (doing it for any other reason than loving your partner and wanting to pledge your love and devotion) has social consequences.

These factors are all subject to speculation and judgment by others, particularly by slut shaming.

Slut-shaming is when you place guilt and subordination on women for their sexuality. Women dressing in revealing clothing, having or being perceived to have slept with lots of people, or even just having a lot of friends who are men are common behaviors women are slut-shamed for.

This is problematic because slut-shaming is sexist and reinforces a sex-negative mindset, based on puritanical sexual values.

Slut-shaming doesn’t give women sexual autonomy, but instead constrains their behavior and choices by placing these expectations on to how they should go about being sexual (i.e., they shouldn’t).

And not losing your virginity in the culturally defined appropriate way can lead to being slut-shamed.

Create a plan

There are many things that you need to remember for the big day and unless you write them down, you will forget. Most people want to make this moment very romantic and unique so maybe you will need to find a place and time that you both like. Also, you may want to decorate the venue and purchase all your supplies including condoms and lubricant.

Next Steps

  • Brook provides free sexual health and wellbeing services for young people in the UK. Brook’s services include local clinics and online digital sex and relationships tool.
  • Chat about this subject on our Discussion Boards.
  • Need help but confused where to go locally? Download our StepFinder iPhone app to find local support services quickly.


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