16 Celebrities Whose ‘First Time’ Was Probably A Lot Hotter Than Yours

Every movie out there teaches us that losing your virginity is a huuuge deal. 

But they mostly show you two ways you can lose it: find a random stranger to have sex with and get it done, over with, finito, dunzo, almost as if this right of passage had no consequences, (STDs anyone?), or…find someone who’s really special (even better if you’re in love), and plan the most delightful evening at a secret hot spot and lose your “V-card” in an epic, almost straight out of a movie scene way.

But there’s a secret option number three, reserved only for a lucky few: dating a celebrity and losing your mind and your virginity to them.

Check out the stories of how these 16 luckier-than-life starlets swiped their V-card in some rather interesting ways.

1. Joe Jonas And Ashley Greene

Sticking to that little promise you made to God must’ve been really hard when you have hot singer actress friends like Ashley Greene, who Joe Jonas reportedly dated when he was 20 years old. Better start praying for forgiveness! We’re pretty sure he’ll understand.

2. Jessica Simpson And Nick Lachey

Well, we all know that Jessica Simpson and Nick Lachey had a somewhat complicated relationship.

She wanted to wait until she was married to swipe her V-card and Nick waited and delivered the most epic wedding night that almost made her forget all about that cheesy “I wanna love you forever” video.

3. Mila Kunis And Macaulay Culkin

Well, it’s safe to say Macaulay Culkin knows how to take advantage of being home alone.

This might be a bit surprising for those of you who slept under a rock during the 9 years Macaulay and Mila Kunis dated. He was her first ever boyfriend at the age of 19, and true to Hollywood’s rich irony, he got to shower her with gifts, attention and flowers, while also deflowering the girl. Yup.

4. Hilary Duff and Joel Madden

It’s no surprise that good girls have a thing for bad boys. If you need more confirmation that adorable old Lizzie Mcguire lost her virginity to Good Charlotte’s Joel Madden, let the girl tell her story in her own words.

“I had a 26-year-old boyfriend … so everyone can make their own assumptions about what I was doing.”

Yeah, we know what you were doing and who you were doing, girl!

5. Taylor Swift and John Mayer

Taylor Swift has a repertoire of mean guys cheating on her, or treating her in a less than stellar way. But she managed to snatch infamous womanizer John Mayer briefly, who was very eager to help her pack her bags and leave Virginville forever.

It obviously didn’t end well and he ended up being the star of one of her songs, “”I Knew You Were Trouble”, that is rumored to be about him.

6. Miley Cyrus and Liam Hemsworth

Miley Cyrus and Liam Hemsworth are one of Hollywood’s cutest, most mismatched couples. They were together for almost 4 years, back when Miley was a hundred times tamer and more centered than today.

She’s never had any issues when talking about her sexual life, so she confessed to losing her virginity to the sexy hunk. No wonder she’s always smiling!

7. Justin Bieber and Selena Gomez

It doesn’t matter how many promises you make to stay pure in Hollywood, when opportunity comes knocking on your door, you just have to let go. Especially when “opportunity,”also known as Selena Gomez, wants to lose her virginity with you.

In true Bieber fashion, he bragged about their ordeal by saying “I knew she was in love with me when she gave me her virginity.”

8. Kim Kardashian and TJ Jackson

Michael Jackson was pretty asexual. We barely got to know much about his sex life, but Michael’s nephews were a different story.

TJ Jackson was the teenager who got to take Kim Kardashian’s virginity back when she was 14. She even got momager Kris Jenner’s blessing… unsurprisingly, who then took the time to teach her about sex. And damn it, did Kim listen!

9. Vanessa Hudgens and Zac Efron

Vanessa and Zack met when she was only 17 years old, and he was 18. They dated for a whooping 5 years where they went steady.

It’s safe to say no one was waiting until their wedding night to get rid of their V-cards, so the whole world knows these two did a little more than dance and sing.

10. Paris Hilton and Randy Spelling

Can you spell “hot”? Paris HIlton definitely can. She lost her virginity in a hotel room to that poor guy that works at Walgreens. Just kidding! It was none other than ultra millionaire heir Randy Spelling, son of Aaron and Candy Spelling.

11. Justin Timberlake and Britney Spears

Justin has never been shy on interviews, but he spilled the tea on what it felt like to date goody-two-shoes Britney, who, according to him, was not that innocent. “She lost her virginity a while a go – and I should know,” he said. What a class act, huh, Britney?

12. Adriana Lima and Marko Jaric

In true model fashion, Adriana Lima shocked the world when she told GQ magazine that despite oozing sex appeal on the runway and practically selling sex every time she starred at a Victoria’s Secret sexually-charged campaign or runway show, that she was a virgin who wanted to “wait”. Up until she married basketball player Marko Jaric in 2009, who took care of showing her the ropes.


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