Shia LaBeouf1

Shia LaBeouf lost his virginity four years ago, when he was 18, but the Transformers star admits the big night quickly became a big mess after he tried to pretend he was more sexually-experienced than he really was.

Shia says his first time took place in a hotel in Montreal, Canada.

In a candid chat with the April issue of Playboy Magazine, he recalls: “For some reason, I was trying to portray myself as a man who had done it (had sex) many times in the past. I didn’t tell the girl I was a virgin.”

“I was all, ‘Don’t worry, babe. I’m gonna handle it tonight.’ And meanwhile I was shaking in my boots.”

“Getting naked was very strange. It was the first time I’d been naked in the light, in front of a girl, with no hiding place,” Shia laughs. “It became apparent pretty quickly that I didn’t know what the fuck I was doing. Somewhere in her mind she had to know.”

“I remember laying her on the bed and putting a pillow underneath her because I had seen that in a porn movie. (It) put her at a weird angle, where I couldn’t get in correctly. I’m not extremely well-endowed. and clearly this wasn’t the move to do.”

Despite their dreadful first encounter, the unidentified victim became Shia’s longtime girlfriend and helped the star master the art of love.

“We had time to work it out. We had a lot of sex and would read the Kama Sutra together and do the wildest shit.”