How I Lost My Virginity: 24 Must-Knows & 15 True Stories That Aren’t So Sexy

Are you thinking about losing your virginity? Or do you want to know what it was like for other people? We have all the tips and stories you want to hear.

When you were younger, you likely imagined that your story of “how I lost my virginity” was going to be the ultimate tale of hot passion, love, and romance. 

Unfortunately for you and the rest of us, the majority of first-timers are more likely to go red-faced about losing their virginity instead of raving about it.

Losing your virginity is a monumental occasion, but that doesn’t mean you’re going to be down for a good time. [Read: Sex for the first time – 37 must-knows & secrets about losing your virginity]

If losing your virginity turned into more of a comedy than a romance, take comfort in knowing you’re not the only one. We’re looking into tips for losing your virginity and tales from those who’ve already had the… err… pleasure.

What people wish they’d known before having sex for the first time

Having sex for the first time is a big deal, and not everyone thinks it through well enough. So, here are some things that people wish they had known before they lost their virginity.

1. You probably won’t orgasm at the same time as your partner, or experience a first-time orgasm at all

Of course, most men orgasm pretty easily. But for women, that’s a different story. It’s not nearly as easy for them to achieve an orgasm. It takes most of them a long time to figure out how to do it right.

So, don’t expect blissful orgasms. And you certainly won’t climax at the same time as your partner. This takes experience – sometimes years of experience – to learn how to do this.

2. It’s okay to talk about losing your virginity

If you’re young, you probably don’t want your parents to know that you started having sex. [Read: True friendship – 37 real friend traits and what it takes to be a good one]

And that’s understandable because you think they might be angry or disappointed in you. But that doesn’t mean you can’t talk to anyone. 

Some parents are even understanding and want to ensure you have safe, protected sex. So, you should talk about it to process the feelings you have as a result. Choose a trusted friend or loved one.

3. Penis-in-vagina sex isn’t the only way to lose your virginity

Usually, people associate “losing their virginity” with traditional, male-female penis-in-vagina sex. While that is how most people have sex for the first time, there are other ways to lose your virginity too. [Read: How to have anal sex and 51 bum must-knows to prepare for your first time]

But gay men can lose their virginity by having anal sex, and lesbians can lose their virginity to a woman too. These days, the definition of “sex” is different for a lot of people.

Straight people think of penis-in-vagina sex as sex. But people of other sexual orientations can define it differently.

4. Not everyone bleeds

There is the expectation that when a woman loses her vagina that she will bleed. And while that’s true for a lot of women, that doesn’t mean that it is for all. [Read: Pop the cherry – what it means and 18 tips to deflower a girl and not hurt her]

Usually, the bleeding happens when her hymen is broken. But a hymen can be broken in other ways other than having sex. For example, using tampons can break the seal in the woman’s vagina too.

5. You will need to prepare with lube

A lot of people are nervous the first time they have sex – especially women. And to get naturally lubricated, there has to be a lot of foreplay so she gets turned on and excited. 

But if she’s too nervous and tense, she might not get very wet. And when she’s too dry, you’ll have to use lube to get in. [Read: 35 slippery good lube substitutes, how and when to use them, and ones to avoid]

So, make sure you have lube on hand just in case you need it. Otherwise, first-time sex will be painful for both people involved.

6. Sex won’t necessarily feel super emotional

Many people assume that sex will bring them closer to their partner emotionally and/or that they will fall in love as a result. While that can be true, it’s not true in all people’s cases.

For some, sex is more of a physical act than an emotional one. [Read: Easy ways for guys to hide their inexperience]

But for others, it tends to be more emotional. Sure, you can bond more after you share such an intimate moment, but it doesn’t mean you’re automatically going to be very emotional about it.

7. Sex isn’t always magical

Many people think that losing their virginity is a magical moment in their lives. We’ve all seen romantic movies where they make having sex look like a fairy tale. But it’s not always like that in real life.

As you will read later in this feature, there are a lot of people who had awkward and even downright bad first sexual encounters. [Read: Awkward signs you’re having bad sex with your lover]

So, don’t expect that when you lose your virginity that it’s going to just be all rainbows and unicorns.

8. Even virgins can have sexually transmitted infections

Many sexually transmitted infections can be passed through oral and anal sex as well as vaginal intercourse. And some infections can even be passed by skin-to-skin contact.

Unprotected oral sex puts both partners at risk for a number of sexually transmitted infections, whether they are giving or receiving genital stimulation. [Read: STDs 101 – the most common types and their symptoms]

The most likely ones are gonorrhea, syphilis, herpes, and hepatitis B. Chlamydia and the human papillomavirus *HPV* are less likely to be transmitted by oral sex, and HIV is rarely transmitted this way,

9. Sex doesn’t change you

Just because you had sex for the first time and you’re no longer a virgin doesn’t mean that you’re not the same person. You’re still you – you just had sex. It doesn’t have to be some life-altering or personality-alter event in your life.

Even if you grew up in a religious household where you were taught to wait until you are married to have sex, that doesn’t make you a bad person.

Sex is a natural and beautiful thing that is shared between two people. [Read: If you’re regularly asking yourself, “Am I a bad person?” read this]

10. You shouldn’t have drunk sex

If someone is nervous about having sex, they might think that having a few drinks – or even a lot of drinks – will make it easier and more pleasurable. But that’s not necessarily true either.

It’s best to have sex for the first time when you are sober. When you’re drunk, most people make really bad decisions. You don’t want to do something that you will regret later. You should go into it with a clear mind and intentions.

11. Sex would take a while before it actually felt good

For most guys, sex feels good right away. It’s pretty easy for them. But for a lot of women, it doesn’t feel good right away.

Their vagina isn’t used to having something so large penetrate it, so it takes some getting used to. [Read: What does sex feel like for a girl & reasons why it feels so good]

Plus, a lot of women are nervous and tense, which causes their vaginas to be overly tight too. Once she learns to relax, she will enjoy having sex a lot more than she does the first time.

12. Your partner is freaking out, too

If both of you are virgins, then you are both probably nervous. Even if just one of you is a virgin, the non-virgin could be nervous too because they want to make it a good experience for the virgin.

So, if you’re nervous, tell your partner. [Read: Sexual anxiety – 25 secrets to not feel nervous about having sex and enjoy it]

There’s no need to put on a brave face if you’re not feeling comfortable. Communication is always important in any relationship, especially when you are losing your virginity.

13. I should have only told my inner circle of friends

If you’re young and in school, you know how gossip can spread. And let’s say a teenage girl slept with a random guy at a party, he might not want to be in a relationship with her or even talk to her again.

That can give her a bad reputation if word gets around that she slept with someone who she wasn’t in a relationship with. [Read: Toxic friends – 22 types, 54 signs, and ways to end friendships that hurt you]

So, you should keep the fact that you lost your virginity to yourself and some close, trusted friends.

14. Sex isn’t just about your partner

A lot of people are so focused on pleasing their partner that they don’t focus on their own pleasure as much as they should. Sure, it’s great to make sure that your partner is enjoying himself or herself, but you should be too.

If you’re a people pleaser, you need to remember this. Your physical and emotional pleasure is just as important as your partner’s. [Read: People pleaser – 21 signs your one and how to stop people pleasing]

15. Sex can hurt in a totally unexpected way

Ideally, sex is a beautiful thing that feels good both physically and emotionally. But it’s not always like that for some people.

Sex can actually hurt physically for some people depending on their anatomy – for both men and women. And not only can it hurt physically, but it can also hurt emotionally too if the relationship doesn’t work out.

16. Honesty is the best policy

Communication is vitally important when you’re losing your virginity. Talk about it beforehand with your partner and discuss your fears and your hopes. They should tell you the same too. [Read: Signs of dishonesty in a relationship that pushes couples apart]

Not only should you talk about it beforehand, but you should also check in with each other while you are having sex to make sure the other person is feeling good.

Afterward, talk about how the experience was for them and what you can do differently next time.

Losing your virginity – other tips you need to know

For those who are thinking of losing their V-cards anytime soon, here are a couple of tips to live by. [Read: Losing your virginity and having sex for the first time]

1. Use protection

She should be on the pill and he should be using a condom, especially if it’s your first time. Using two types of contraceptives is the safest way to have sex, aside from abstinence. [Read: Common birth control methods, 25 pros, cons & ways to pick the best one]

2. Don’t ever have sex because you feel pressured to do it

If you’re young and don’t feel ready to have sex yet, don’t do it just because your partner wants to or if you feel peer pressured. Do it when it feels right to you – and only you. [Read: Date rape – facts, signs, and what you must do ASAP]

3. Have sex with someone you trust

You definitely don’t want to lose your virginity to a stranger or even a one-night stand. Make sure you’re in a relationship with someone you trust and you love – and loves you back.

4. Ladies, make sure you’re completely aroused and wet before attempting intercourse.

Before the act of penetration, ensure you are lubricated well, either naturally or with the help of lube. You may even want to orgasm before actual penetration via oral or hand stimulation. This will help ease any pain from tightness or friction. [Read: First-time sex and myths girls should quit believing]

5. For women, have your partner rub your clit, or use a vibrator on yourself during intercourse

The clit is full of thousands of nerve endings but isn’t directly stimulated through intercourse. This is why your hand or a sex toy is always handy. It will relax your body and make you feel good! Plus, this will give you a better chance of having an orgasm.

6. Men, take your time

You might even want to practice holding back ejaculating when jerking off in preparation for the big day. Hey, it’s your first time, nobody’s expecting you to last an hour, but 10 minutes would be pretty awesome for your lady love.

7. Make it comfortable

You don’t want your “how I lost my virginity” experience to be you shagging in the back of a smelly van or rushing it in the basement before your parents come home. 

While you don’t have to recreate a romance novel, at least try to make it romantic for the other person involved. And let them know you appreciated sharing that moment.

8. Don’t stress! 

Sex sucks at first, but after some practice, it’s going to be amazing. Make sure you’re open with your partner about what turns you on, and you’ll find sex is going to be your new favorite hobby. [Read: First-time sex and the virgin’s guide to nailing it]

First-time sex stories – the good, the bad, and the very ugly of how I lost my virginity

Want to see how your virginity story measures up? Here’s a collection of 15 true “how I lost my virginity” stories for your enjoyment.

How I lost my virginity – the good

1. I lost my virginity to my high school boyfriend when I was 17. He was really sweet and knew I wanted to wait, so after about a year together, it finally happened. 

We were making out in his basement, and finally, we just did it. It was only about 10 seconds long, but it was sweet while it lasted. –Trish H. [Read: The virgin’s guide to acting like she has experience]

2. I lost my virginity to my wife, and I couldn’t be happier because of it. My friends busted my balls when they found out I’ve only ever been with Sarah, but I prefer it this way. 

I like the security that comes with only being with one girl and knowing we’re both in a committed relationship – not a high school one. To me, nothing beats that. –Derek L. G. 

3. My first time was actually with my husband. We waited until we were married to have sex, and we are both the only person each other has been with. It’s been amazing. [Read: First-time sex and the male virgin – 21 secrets to feel like a pro in bed]

I hear some of my girlfriends complain how their new boyfriend doesn’t please them like their last one.

While it sounds embarrassing in this day and age to say that I’ve only been with one man, I’m so happy to know I will never have the same problems my girlfriends have. 

My husband is the only one who’s ever touched me and vice-versa, so we were able to train each other to do exactly what we liked. [Read: The virgin’s guide to acting like she has experience]

Our first time was romantic and perfect, with dozens of candles and lots of kissing! –Alexa 

4. I lost my virginity when I was 18 to a girl I knew was going to be very special. We got to it quickly, after only about a week together. We did it in her bedroom while her parents were both at work.

I fumbled around awkwardly, and I know she didn’t enjoy herself because she was blunt enough to tell me so. She got pregnant right away.

I know this sounds like a disaster, but I was head over heels for this woman and I still am. We’ve been married for 22 years now. –Ron S.

5. I had sex for the first time on a drunken camping trip when I was 19. I slept with my best friend in the back of a truck at the campsite, and I’m not even kidding, a raccoon jumped up into the vehicle while we were going at it.

It was definitely unforgettable, but probably not for the right reasons! Looking back, I was such a rambunctious person, I’m glad my first time was eventful and different. –Marissa L. [Read: On losing your virginity to a one night stand]

How I lost my virginity – the bad

6. My first time happened with a guy I met at a frat party. I was a college freshman and desperate not to be a virgin anymore. 

I had all these notions that sex was going to hurt, and I’d be bleeding so badly I’d need to be cauterized by the end of the night. Neither was true!

Sex didn’t hurt, it just felt like nothing, unfortunately. Looking back, I wish I hadn’t been so concerned with my virginity and had waited to lose it to someone special. [Read: 50 best steamy romance movies to get you both hot, naughty, and in the mood]

Instead, I had a quickie with some dick I awkwardly bumped into for the rest of my college years. –Tiffany E.

7. I slept with my high school girlfriend before she went to a sleepover. It was all extremely awkward, especially when she informed me that she had her period and asked if I was still up for it. 

I didn’t want her to change her mind about taking this step with me, so I said that was fine. I suited up with a condom and away we went. We didn’t want her parents to know we were having sex. [Read: 15 painfully embarrassing things that can happen during sex]

This all went out the window after they saw the graphic mess we left on her bed sheets. Great experience, but a disgusting result. –Kevin B. 

8. I was actually that girl whose first penetration experience was anal. I thought I loved the guy, but I wasn’t sure if I wanted to give him my virginity so, in the ass we went. Yes, I know, cliché.

He got me plenty excited beforehand, and we used a ton of lube. He touched me while he went at it and to my great surprise, I finished. [Read: What does anal sex feel like both physically and emotionally?]

I really wish anal wasn’t my first penis-in-my-body experience since it sounds so trashy, but I was pretty glad I never wasted a hymen on that guy. Ugh. –Mel P.

9. I was 18 and just about to graduate high school for the first time. I already felt like a late bloomer since I was still a virgin, and it didn’t help that my boyfriend at the time had been pressuring me for months to have sex. 

At this pre-graduation party one weekend I decided to get completely drunk and finally gave in to him. [Read: Sex for the first time – the teen’s guide to a great time]

I just remember how much it hurt and me crying myself to sleep when I got home, and I didn’t feel closer to him or any more adult. 

I just felt nothing. If he was really the one I wouldn’t have needed to get so drunk, nor would he have needed to beg for it. What a waste. –Brit C. 

10. My first time with my boyfriend was pretty uneventful. I was actually 23 the first time I had intercourse and it was, meh. I loved the guy so that was special and everything, but to be honest the sex didn’t feel like much. [Read: Puppy love – what it means, stages, 37 signs, and ways to turn it into real love]

He was on top and finished pretty quickly. I could tell he was embarrassed and he said we would try again when he got his hard-on back. Luckily, it gets a zillion times better after the first time… and the second… and the third. –Maggie C.

How I lost my virginity – the ugly

11. The first time I had sex was with my girlfriend in high school. We were both 17, and we did it in her parent’s bed when the house was empty. 

I remember she had Lost *the TV show* playing in the background in case anyone came home. [Read: The rules of spending the first night together]

I got on top, but I was really gassy, and when I started getting really into it, I was thrusting faster and farted about three times. My girlfriend looked stunned and then busted out laughing. 

My dick shriveled up so fast I couldn’t even look at her. I’m pretty sure I cried for 10 minutes after, and we didn’t have sex again for weeks. –Aaron T.

12. My first time was with my college boyfriend. We dated for seven months long-distance and had known each other since high school. [Read: Long distance relationship – 46 LDR tips to make it work and not screw up]

I came home for the summer and decided I wanted to lose my virginity to him. He was so nervous he could barely stay hard.

Eventually, he got inside of me, but his penis felt rubbery, gross, and small. He finished after about a minute. 

Later, I found out that the reason he was so nervous was because he already had a girlfriend – of three years. He was cheating on his girlfriend with me, unbeknownst to me.

He dumped me the next day, told his girlfriend he’d been cheating on her, and they stayed together for another year after. It was a horrible experience altogether. I have literally never seen him since. –Becca M. 

13. I was about 17. We’d fooled around before, but this was the big one. I had always thought I’d plan something special for my girlfriend, but instead, one night she just said, “Let’s just do it” and so I attempted to put it inside her.

But my nerves got the best of me, and I couldn’t even stay hard. This went on for what felt like forever. 

When I finally managed to get inside her, her 6-year-old cousin barged into her room. It was scarring for all parties involved, I’m sure. –Brian L. [Read: 29 best sex positions and tips for small penis owners to go deep and hit the spot]

14. My girlfriend and I were both at university and decided to do the deed on our first anniversary. 

I got a fancy hotel room for the night and we had a nice dinner, watched a movie on my laptop in our hotel room, and then got down to business. We were both virgins, so I wanted everything to be special for her.

I knew a first time for a girl usually isn’t the best, so I wanted to make sure she had an orgasm via my hand or mouth. [Read: How to eat a girl out – 81 oral sex tips to eat pussy and tongue her to bliss]

Unfortunately, she didn’t want my hand or mouth… or eyes, come to think of it, anywhere near her nether regions. She told me I wasn’t allowed to look at it – period.

Despite me telling her I thought every part of her was sexy and beautiful, she still wouldn’t let me look or touch. Needless to say, this made blindly inserting my penis for the first time quite the challenge. –Jason T. 

15. I lost my virginity when I was 18. I was really Catholic at the time and felt really strange about my decision to sleep with my boyfriend. 

He had a ridiculous on/off relationship with his ex-girlfriend and part of me worried that he would go running back to her whenever she called. He assured me that wasn’t true and finally, we slept together in his bedroom. [Read: 32 reasons why you love someone, the psychology of love, and why it exists]

His dad came home halfway through and kept yelling for my boyfriend, asking him if he’d taken out the trash. He came and knocked on the bedroom door and kept talking until he realized that we were, well, in a compromising position.

We laughed about it at the time and my boyfriend was super sweet after. Unfortunately, he left me for his ex about three days later. Yep. Days. Don’t give it up to someone who you know you can’t trust. I regret it completely. –Emily A. 

[Read: 25 hilarious myths about sex most of us used to believe]

Sometimes your ‘how I lost my virginity’ story isn’t always the romance novel you’d hoped for. Just know that you’re not the only one who wished they’d waited, or that they could block their first-time memory out forever.