How I Lost My Virginity: 15 True Stories That Aren’t So Sexy

First times aren’t always so magical. We’re looking at 15 how I lost my virginity stories that’ll either make you jealous or make you cringe.

how i lost my virginity

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. Especially if you’re female. Unfortunately for you and for 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. 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.

Losing your virginity – The tips you need to know

While 75% of men report climaxing during intercourse, only 29% of women achieve orgasm. For females, this number is going to be much, much, much smaller during her first time. For those who are thinking of losing their V-cards anytime soon, here are a couple 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. Backup = safe.

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

#3 Have sex with someone you trust.

#4 Ladies, make sure you’re completely aroused and wet before attempting intercourse. You may even want to orgasm before actual penetration via oral or hand stimulation. [Read: First time sex and 7 myths girls should quit believing]

#5 For women, have your partner rub your clit, or use a vibrator on yourself during intercourse. 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 female involve. And let her know you appreciated sharing that moment together.

#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.

#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. [Read: The virgin’s guide to acting like she has experience]

#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. 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. 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 camp site, 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 have been so concerned with my virginity and had waited to lose it to someone special. 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. This all went out the window after they seen the graphic mess we left on her bed sheets. Great experience, disgusting result. –Kevin B. [Read: 15 painfully embarrassing things that can happen during sex]

#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. I know, 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. 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 my first time. I already felt like a late bloomer since I was still a virgin, and it didn’t help that 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.

I just remember how much it hurt and me crying myself to sleep when I got home. 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. [Read: Sex for the first time – The teen’s guide to a great time]

#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.

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 second… and 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 10 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. 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. [Read: The curious guy’s and gal’s guide to anal sex for the first time]

#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 in her room. It was scarring for all parties involved, I’m sure. –Brian L. [Read: Sex with an uncircumcised man – the myths and all]

#14 My girlfriend and I were both at university and decided to do the deed on our one year 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. 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. [Read: How to get a girl to have sex with you in 10 steps]

#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.

His dad came home half-way 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.

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Waverly Smith
Waverly Smith is a freelance writer who has been getting paid for spreading her sarcastic take on love, life, and sex since 2010. She is many things that people...
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