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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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1,812 Responses to “Leonardo DiCaprio's Teenage Hookup Detailed in New Memoir”

Pages: [1] 2 3 4 5 6 773 » Show All

  1. 1
    hey there! Says:

    HAHAHAH lol, are you meditating Leo?

  2. 2
    HAHA12 Says:

    LMAO reminds of×435.jpg

  3. 3
    LOL42 Says:

    He looks great

  4. 4
    LOL42 Says:

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

  5. 5
    Leokas Says:

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

  6. 6
    mlllllllllllllllllllllef Says:


  7. 7
    Leokas Says:

    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! ;)

  8. 8
    HAHAHAHA Says:

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

  9. 9
    V Says:

    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!

  10. 10
    Zzzzzz Says:

    @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! ;)

  11. 11
    HAHA12 Says:

    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.

  12. 12
    baby Says:

    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.

  13. 13
    HAHA12 Says:

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

  14. 14
    Leo Says:

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

  15. 15
    cupcake Says:

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

  16. 16
    also... Says:

    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.

  17. 17
    Weird Leo Says:

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

  18. 18
    Black sharpie Says:

    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?

  19. 19
    Leokas Says:

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

  20. 20
    HAHA12 Says:

    @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.

  21. 21
    #### Says:


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

  22. 22
    also... Says:

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

  23. 23
    Tobey Maguire Says:



  24. 24
    @Leokas Says:

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

  25. 25
    HAHA12 Says:

    @Tobey Maguire:

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