Grownup Guide to Losing Your Virginity
It doesn’t have to suck
I was 16 when I lost my virginity and I soon found out I was an outlier.
Not because of my age — it was standard enough to start screwing right around the time you were old enough to drive — but because of how enjoyable it was.
Hearing other people talk, it was like losing your virginity was something you did as a rite of passage and as a gateway to enjoyable sex in the future, not because it was actually pleasant. At best, it was a doorway to enjoyable sex, somewhere in the future.
They talked about wincing through the pain.
They talked about discomfort and confusion.
And they talked about bleeding — often quite a bit of it.
They also talked about all this as if it was natural and unavoidable. “It’s supposed to hurt your first time” was something everyone just kind of knew — no one had a clue where they heard it from, but they were dead certain it was a fact.
But I knew it was a lie because when my boyfriend and I decided to have sex for the first time, it wasn’t painful at all.
Somehow, even though we were both inexperienced and a little naïve, we managed to hit on the formula for pain-free, comfortable, and highly pleasurable sex.
After hearing about so many terrible first times, I wanted to whisper those secrets to everyone I knew.
I also put my knowledge to good use. On two more occasions, I was the girl some young guy lost his virginity to. I loved being their first. I liked the look on their faces as soon as their cocks were in me — making contact with pussy for the first time. Their surprised grunts of pleasure gave me a real thrill.
But what I liked most of all was teaching them. I loved helping them go from innocent, surprised boys to confident guys who know a thing or two about fucking.
Unfortunately, I’m a little too old for that kind of hands-on education now. (I have no problem being a cougar, but I’ll need my cubs to be a bit older.) So, instead, I’ll settle for giving advice. If I can help anyone out there have a fun first time just like I did, I’ll be one happy writer.
I can’t pretend to be an expert at this — like everyone else, I only got to lose my virginity once — but I’ve had a lot of thoroughly enjoyable sex over the years, and with these tips, I’m hoping others can, too.
You Need Trust, But Not Necessarily Love
The number one piece of advice I heard on this subject (okay, after “use protection”) is to make sure you’re with someone you love.
Wait until you’re in love and all the pieces will fall magically into place.
Well, no, not quite. Love is nice, but in this case, it’s not always needed. You can have great sex with someone who just like, or love as a friend, or love but don’t love love. Just because you’re not hearing wedding bells whenever they text you doesn’t mean it’s not the right person for you to have sex with, even for your first time.
You can also have some pretty bad sex with someone you love. Being in love doesn’t mean you’ll know what you’re doing.
What you really need is to be with someone you trust, someone who makes you feel safe and cared for.
Trust matters because you need to know the person you’re with is going to respect you, care about you, and is in it for your pleasure, too, not just theirs.
I thought I loved the guy I lost my virginity with, but he didn’t really love me, not in any major way. The relationship didn’t last much longer. But I have no regrets. It was fun, it was safe, and it didn’t have to be happily ever after.
Work on Your Communication Skills
For any kind of sex, communication is the biggest skill you’ll need.
Not some weird positions you saw online or read about in the Kama Sutra. Not tracing the alphabet on the clitoris with your tongue (guys, please, where do you pick up this nonsense?) Not even the Kivin Method.
Nope, just plain old talking, listening, and attentiveness.
Being able to express what you like, what you don’t, and knowing how to read each other’s body language for signs of discomfort is paramount.
Sex is best with someone who is responsive to your cues. Someone who knows how to check in with you, see how you’re feeling, and adjust when things aren’t going the way either of you thought they would.
If you’re not quite there yet, create an open dialog and some close communication with the person you’re planning to do it with. Even if you just hang out and talk — it can make a huge difference.
Arousal Matters
I know I sound like Captain Obvious when I tell you that you should be aroused before you start fucking, but it’s not always a given.
You might be nervous or downright panicked for your first time, which might keep you from getting right and properly horny.
A lot of people also feel more impatient than horny when they decide to lose their virginity. It’s a band-aid they’re eager to rip off, not something they decide to do because the moment feels right.
Take your time to get aroused — to arouse each other. If you’re nervous, it might take a while, but you will almost certainly get there.
Arousal isn’t just important because it makes sex more exciting — it’s also a way to make it a lot less painful.
Your body provides you with natural lubrication when it’s aroused, and that’s an important part of pain-free sex. But it’s not the only one.
Let me tell you about the cervix, because a lot of sex talk and sex tips focus on the clitoris, the labia, and the vagina, but the cervix needs some attention, too. The funny thing about the cervix is that, unlike the clitoris, you want it out of the way. Getting it out of the way takes physical arousal.
Arousal causes blood to flow to the vagina, which causes the vaginal canal to elongate. When that happens, the cervix moves up and, importantly, out of the way.
Just wanting sex, then, isn’t enough to make sure it’s pleasurable. Non-aroused sex is painful in part because the cervix is in the wrong position. So, make sure you have time to get in the right mood.
Get All Your Supplies Ready
Chances are, you already know that you should have condoms handy. And I do mean it when I say condoms in the plural. If things don’t go that great on your first try, you might have to go a few times. And if things go really well on your first try, you’ll want to go at it again — and again.
I’m not saying you have to buy in bulk, but make sure you have at least three or four.
And then there’s lube.
When I was a teenager, lube had a weird reputation. It was the kind of thing people would bring up in jokes, not the kind of thing you were really supposed to use. Lube was somehow for perverts (and people meant that in a bad way), and unless you were going to have anal sex, it was pointless.
Oh, how wrong we were.
Listen, lube is amazing.
The one thing I don’t want when I’m having any kind of sex act is friction. I want everything to be as slippery as possible so I can get maximum enjoyment. There’s nothing lube can’t improve, no matter how wet I am.
And yeah, like just about every other girl out there, I’m no stranger to spitting into my palm before giving a hand job (you’re in the car, what else can you do?), but it’s no substitute for the real stuff.
You don’t just want your first time to be okay. You want it to be damn good, and you want to minimize as much physical discomfort as you can. So, make sure you have some lube on hand.
Condoms and lube are your basic first-time sex gear, but make sure you prepare anything else you plan to use. If you and your partner are on the kinkier side, keep whatever accessories you need within close reach so you don’t have to interrupt the flow because you need to dig through your drawer to look for your handcuffs.
Don’t Have a Pre-set Idea of What Counts as Sex
If you would have asked 15-year-old me how to lose your virginity, I would have probably told you that it involved some kissing, undressing, and guy-on-top missionary.
(What can I say? I wasn’t born dirty.)
But then, when it was time to actually do the deed, I discovered there were a lot more options to work through, a lot more discussion as to what, exactly, we would do.
Be ready to try things out, to experiment, and even to talk through what you want to do in real-time.
There’s no rule that says you have to skip straight to penetrative sex after a bit of foreplay. If you’d rather give or receive oral first to work your way up to it, that’s just great.
And even though you won’t see it depicted in soft-focused romantic movies, there’s nothing wrong with playing around with a little tit-fucking before the big act.
And speaking of the big act, no one says you have to end there. You can keep doing whatever playful things you want to after you’ve fucked.
This might not apply to most people, but no one says you have to lose your virginity in couple sex. Having your first time with more than one person can be just as special and amazing.
Plus, I always like bringing a friend along when I try new things, and I doubt I’m alone.
The point is there’s no playbook here. You have to write your own, and it should reflect what you and your partner(s) really desire, not some preconceived idea of what romantic or special sex should be like.
Be Ready to Stop (and Start Again)
I feel like I’ve said this about a hundred times already, but it’s worth repeating again: sex should be comfortable. Heck, it should be a lot more than just comfortable.
If anyone is uncomfortable or experiencing pain, just stop, take a step back — whether that means using your hands and mouths again or even just kissing for a while — and then try again when you’re ready.
Sometimes, it just takes a little more foreplay to get in the right zone. Or it might just take a few more minutes to get used to being naked with each other and take the nervousness away. Sometimes, the stress makes it hard to get it up or keep it up.
Whatever it is, there’s no shame in working your way back up to penetration.
And if it just isn’t working no matter what you try — if you just can’t get to a place where it feels really good — it’s fine to stop. Just watch Netflix and (actually) chill for the rest of the night and try again another day.
Block Off the Entire Day
I’ve heard from so many people who have lost their virginity in a rush.
When my husband lost his virginity (not with me — sadly, I missed that opportunity), it took him so long to work up the nerve. When he finally did, the sun was rising and he didn’t feel like he had a whole lot of time left to actually get frisky and fuck.
A quickie’s fine when sex is old hat, but if it’s your first time, you’ll want to block off the whole day.
Like I said, you need to get comfortable. You need to get aroused. You might need to stop and start and stop and start and stop and start…
And when you do end up fucking, you might want to do it again. And again. And again.
It’s more common these days to say that losing your virginity isn’t special. But you only have one first time, and you’re entering a new phase of your sexual life. So, make a day of it. Whether you want to have foreplay for hours, fuck seven times, or just lay in each other’s arms after, make sure you block off enough time to make it happen.
Set the Right Tone for Your Sex Life
My first time set the tone for my whole sex life.
I was already quite sexually inclined before I even came in spitting distance of a nude body. But having an amazing first time cemented me as a life-long fan of all things sexual.
Not everyone is so lucky. And I can’t help but wonder how many of our hang-ups or negative attitudes surrounding sex can be traced back to one miserable night that leaves you asking whether it ever gets better.
Young people need more preparation than just being told to use a condom. They need to have the tools and knowledge to make sex feel good, even the first time.
And all it takes is communication, attention, and enough time and care to do it at your own pace.
Oh, and lube. Lots of lube.
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