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Leonardo DiCaprio's Teenage Hookup Detailed in New Memoir

Leonardo DiCaprio's Teenage Hookup Detailed in New Memoir

Leonardo DiCaprio takes a moment to bask in the heat of the sunlight while waiting for his car to arrive on Saturday (November 16) in New York City.

The 39-year-old actor allegedly had a one night stand with video vixen Bobbie Brown back when he was only nineteen, and now the hookup is being detailed in her new memoir “Dirty Rocker Boys: Love and Lust on the Sunset Strip.”

“I unbuttoned his jeans and tugged down on his boxers,” Bobbie, who was twenty-six at the time, wrote in the book (via The Daily Mail). “(What) I saw made me gasp. It made no sense. The kid put Tommy Lee to shame.”

“Waves of satisfaction rippled through my body. If only Tommy Lee could see me now. He was a unicorn. Rare, innocent, and horny. Me, on the other hand, I’d been engaged, married and had given birth. I needed a man, not a man-child,” she added.

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Photos: SplashNewsOnline
Posted to: Leonardo DiCaprio

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  • hey there!

    HAHAHAH lol, are you meditating Leo?

  • HAHA12
  • LOL42

    He looks great

  • LOL42

    LMAO. Good one right down to the facial hair. I wonder if it was deliberate??

  • Leokas

    Lukas here, my baby sure loves his Vitamin D but, he sure loves my D more… ;)

  • mlllllllllllllllllllllef


  • Leokas

    That Bobbie Brown girl her is right, Leo sure has the monster D, but unlike her and Toni and the rest of dem models, IT’S MY D! It has Lukas written all over it! ;)


    Omg what the hell are you doing. You’re so embarrassing lmao.

  • V

    He looks so good! He needs to spend more time in the sun than in clubs. LEO, THE SUN LIGHT IS BETTER THAN THE CLUB LIGHT!

  • Zzzzzz

    @HAHA12 & LOL42: jumping back on for a sec. Leo looks great! Also looks like he is going on a trip. Maybe Austin after all?
    I’m off again! ;)

  • HAHA12

    Every time he get caught on camera he does something funny. I can always count on him to make me laugh, intentionally or not.

    Also forgot to comment on this earlier but LMFAO at him singing Waterfall to Bobbie Brown. I can just imagine it.

  • baby

    Who hasn’t Leo slept with???? He’s a major ho and slu and it’s sad he gets praised for it. Double standards. He’s STD ridden. And ppl think he’s going to get married to a smart sophisticated woman and have a cute little family and be faithful, YA RIGHT! Leo is like every other man, actually worse.

  • HAHA12

    Hey :p Yeah he looks skinnier here and it looks like his hair is shorter?

  • Leo

    = future embarassing dad w/ a 21 year old wife :’(

  • cupcake

    Leo looks like how he did 10 yrs ago, like around that gangs of new york time thingy, hot

  • also…

    I see Lukas on one of the photos! Maybe he us going to Austin after all and Lukas grew up there…
    Leo looks good on these photos.

  • Weird Leo

    Leo is such a weird guy, he does the strangest things in real life

  • Black sharpie

    He looks good here. I can’t get over that one day he looks so bad and the next day he looks great. Lukas is there(of course!). Maybe it’s a quick boys getaway? Does anyone know who the two other guys are in one of the pics?

  • Leokas

    Leo and I hooked up in the backseat of the car! Shhh, don’t tell anybody ;)

  • HAHA12

    @Black sharpie:
    His looks fluctuate too much. He goes from looking great one day to looking horrible the next, its weird.
    And yep I just spotted Lukas in the hat! Leokas must be enjoying these pics lol.

  • ####


    He does look good but his hair is slicked back and looks greasy or maybe it’s just wet. :-)

  • also…

    @Leokas: Your secret is safe with me! ;) You love your precious unicorn, don’t you!

  • Tobey Maguire



  • @Leokas

    Tell us what goes down in Austin Leokas darlin’.
    Safe trip and no hanky panky on the plane now

  • HAHA12
  • Alaia

    Be free, Leo. Be free.

  • poo


  • Donatella Versace
  • huh?

    Leo trying to forget the embarrassing events of the past week? Same here!

  • Zzzzzz

    @####: Hey! Only on for a sec – I think it’s wet. Leo rarely every gels his hair back when he’s just out and about. Either way, he looks really good! ;)
    Re the article: if you read the entire section of this article, Bobbi admitted that they never actually had sex. She said she stopped after he started asking her if she had any stds and she was also freaked out about the age difference. She is definity using Leo’s name to get publicity for the book.
    I’m off again!;)

  • Zzzzzz

    Typo * rarely ever….

  • also…

    @Zzzzz: If you read the part about Leo in the Page Six article she said ‘we had sex.’
    @huh?: LMAO! He can try…

  • Black sharpie

    I think there was also a version of this story where she says,” he put a condom on while I went down on him”. Not exactly sure how that’s possible but whatever.
    This woman is trying to sell her book and Leo is her best shot at doing so.

  • ####


    Too late!! It’s already out in the universe!!! LOL

  • Zzzzzz

    @also…: interesting because in another article she said they ended up not having sex. Guess she couldn’t make up her mind? Lol!

  • Black sharpie

    Unfortunately, those birthday videos cannot be unseen!

  • ####


    I figured it was wet. Sounds like she’s definitely using Leo’s name to sell her book but it’s definitely an interesting story! LOL

  • Ah

    LMAO. Poor drunk, clueless Leo must of thought there’s no way those vids would of leaked everywhere.

  • ####


    Oh and I forgot to answer you last night about Disneyland, unfortunately the trip has been cancelled. :-(

  • also…

    @Zzzzz: This is what was posted in the Post.`… and then we had sex…`

    “I’d just been with Tommy Lee, but Leo looked huge. After that, he put on a condom while I went down on him and then we had sex. But the whole thing was awkward, and we didn’t hang out much after that.”

  • S

    Hello Handsome!!!

  • ####

    @Donatella Versace:

    Wouldn’t be surprised if they had a one night stand! LOL

  • Zzzzzz

    @also….: thanks for that. When I get off work, I’ll try and find the article that said they didn’t have sex.

  • Emmy Rossum
    I wonder what he whispered to her! Probably something flirty. He should go for girls like her.

  • stache

    What’s with the mustache? He’s about an inch from a John Waters.

  • Amy


    I find her story hard to believe. I think Leo is the type of guy who would have everyone sign a confidentiality agreement first.

  • Zzzzzz

    @Amy: I’m not sure about that. Remember he was only 19 at the time. This was before Leo was huge. He was much more open. He didn’t get secretive until after Titanic.

  • BeardClub

    There’s a pic of LD fully frontal nude taken on a yacht when he was with Giselle. He’s even got a b o n/e r and it’s not big at all, just average and uncircumcised. Just google him n/u/d/e and you’ll see it. Not impressive at all.

  • ####


    I thought that pic was a hoax or photoshopped or something.

  • @beardclub

    im pretty sure that picture was fake and photoshopped, also the torso doesn’t really look like his either.