In the April issue of Playboy Magazine, Shia LaBeouf shares the story of when he lost his virginity four years ago at the age of 18 in a hotel in Montreal, Canada.

He says:

“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. 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.”