Shia LaBeouf almost ruined his first sexual encounter by pretending to be a know-it-all playboy. The actor lost his virginity four years ago, when he was 18, and admits the big night was a mess, comprising of bad lines and embarrassment.

In a candid chat with the new Playboy magazine, the actor 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."

LaBeouf, 22, confesses his first time took place in a hotel in Montreal, Canada, adding, "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 f**k 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."

However, the embarrassing night had a huge upside - the girl in question became a longtime girlfriend and she helped LaBeouf become a much better lover.

He adds, "We had time to work it out. We had a lot of sex and would read the Kama Sutra together and do the wildest s**t."

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(This news article provided by World Entertainment News Network)