Jessica & Ashlee Simpson sunbathe their breasts

July 14th, 2008 // 76 Comments

Jessica Simpson and her sister Ashlee sunbathed on a yacht while watching Tony Romo perform in a golf tournament at Lake Tahoe. Meanwhile, below deck, Joe Simpson flushed the GPS down the toilet and cut the fuel lines. Best family vacation ever!

EDIT: Okay, so the chick in the red is not Ashlee Simpson. My bad, I saw the nose and went with it. However, I just added pics of Ashlee on the S.S. Boobieprise. Though I can’t be certain until my man on the inside gets back to me with the ultrasound. C’mon, Papa Joe…

Photos: Flynet

  1. kristin

    Cute dog.

  2. Nando

    That’s not Asslee next to Jessiwhore. I don’t know who that other girl is.

  3. Jackie

    The woman in the red is not Ashlee…. idiot…….

  4. Um, Ashlee had a shotgun wedding because she’s PREGNANT, remember?

  5. fgjk

    MOTORBOAT….and Im talking about the titties, not the actual motorboat

  6. don

    jessica has the biggest horse-mouth ever. just look at the last few pics.

  7. Bleh

    Why the Nazi salute in the last photo? Is Romo a skinhead and had converted Jessica?

    To the artbellmobile!

  8. Jen

    the girl in the red looks nothing like ashlee thats not her

  9. Jen

    the girl in the red looks nothing like ashlee thats not her

  10. AJ

    Jessica is getting fat again. She is wearing a fat ladies swim suit. She is so desperate for love. When she was married to Nick; she hated sports and now she is dating a football player and attending his football games and following him around like a lost puppy. Jessica was not into golf either and now she is desperate for love so she watches golf. She got a big fat head and thought she could do better than Nick and now she is just a pathetic loser when it comes to love. She was John Mayer’s easy booty call. She has no talent and will eventually fade away. She had to get breast implants because she lost a lot of weight for her failed movie, and got saggy and needed implants to get perky again. Jessica should have just waited until she gained all her weight back to get her breasts perky again. Jessica is one ditzy boring loser.

  11. don

    the Nazi salute is just coincidental because if you look at the previous pics she’s just waving in all sorts of different ways.

  12. e

    I would have to repeat what everyone has already been saying, namely: “That bitch in the red swim suit is NOT Ashlee, IDIOT!”

  13. steve

    with romo’s salary and popularity, he could definately do better than this chunky monkey. I mean sure she has nice tits, but lets face it they will start sagging soon, if not already.

  14. Vince Lombardi

    No, no, no…. The bitch in the fur is “Ashlee.” The bitch in the red is “Spot.” See, she’s got a really freckle-ly chest area… so she would be… um… “Spot?” oh, fergit it. Where’s Winehouse?

  15. whatever

    AJ= Nick Lachey…
    Maybe you should take some Midol?

  16. c’mon people. idiot?? so what if it’s not ashlee. she’s got the same size nose and looks like she has the same vapid personality. so what’s all the beef about.

  17. krystal

    thats not ashlee..

  18. megan

    that looks NOTHING like ashlee haha how could you even think it does?

  19. AndrewMacCloud

    Looking good, have a nice Vacation Tits, Champagne for everyone!.

  20. JJ


    She use to have nice perky tits but lost a lot of weight and her tits got saggy so now she has breast implants to make her saggy tits perky; nothing special about breast implants.

  21. In picture 6, that dog looks like it would rather jump than be subjected to that kind of idiocy.

  22. Moses from the Mount

    You think Jess does Anal? I could really get used to grabbing those bit o tities while riding her ass.

  23. What a stupid fucking hat. Why don’t people know how to dress anymore? Is she taking lessons from Britney? Fedora’s are for MORONS!!

  24. DP

    It’s nice to see #18 Megan and #3 Jackie take their B List celebrity sightings so seriously. They must be really ugly.

  25. Jumpin_J

    I think we’re all missing the point that she’s sunbathing on a boat… with her bikini on. C’mon Jessica. Daddy’s downstairs disconnecting the ol’ fuel line, if you know what I mean. Take your top off. Nobody’s looking, honest.

  26. passerby

    The lady in red is her mother!

  27. steve

    #20 I wasn’t aware that Jessica has implants. Thanks!

  28. no

    20 – you don’t know anything. those aren’t implants

  29. miserable

    I wish she would let those sweater cannons loose in playboy and put a triumphant end to a crappy career.

  30. jay

    if she ever did playboy I would buy a dozen copies because I’d jizz all over them pics.

  31. omnibacon

    geez I wish just for once she would shut that giant yap. constantly ruining a great set of cranks

    how do people around her refrain from just randomly punching her in the head?

  32. allison

    Heh, that’s not ashlee.

  33. sammy

    omnibacon, I agree with you. You know that 90% of the time he spends with her is with his cock down her throat just to shut her up.

  34. sammy

    Tony Romo that is…

  35. 100% real, no doubt about it.

  36. poirot

    that’s not ashley either…

  37. havoc

    #22…good call Papa Joe was probably first to tap that ass. Nick probably got stick it in her pooper b/c he told her he loved her. And I get the feeling anal sex is nothing new to Romo the Homo…..


  38. Where's Darkwing Duck?

    Sometimes the only way to shut a girl up is to stick something in their mouth. However, I get the feeling Jessica would keep making noises. Hopefully they are the humming sounds most men enjoy with a MMMMM HMMMMM when they tell her they’re going to come.

  39. Leo

    :O who is that ugly guy on the boat? =O

  40. JimmyBachaFungool

    Did anyone notice that’s not Ashlee?

  41. really?

    #40… please see posts #1 through #39 above.

  42. Maurice

    I like my ladies fat like Kim Kardashian. Fat on the ass, fat hips, and fat thighs is all sexy fat plump soft meat and a treat.

  43. boo

    You can see the top of Ashlee’s poorly dyed head in the pic with Pete Wentz in it. Yep, it’s still that hideous orange.

  44. Tony Romo

    I hate the way people think I’m a homo.

    It distracts me when Terrell gives me a hummer.

  45. Miserable Bastard

    If someone was to point out the elusive chicken of the sea to Jessica, and she “accidentally” fell over the boat’s railing while trying to spot it, would she sink or swim? The solid block of concrete between her ears would try to drag her straight to the bottom like an anchor, but her built-in flotation devices would valiantly resist.

  46. Kim Lardassian

    Ugly fake titted bitch, bimbo brainless vapid moronic c*nt. I don’t like her.

  47. Ted from LA

    I’ve been thinking about the lady in the red and it turns out I don’t give a shit who she is.

  48. PwincessSanitaryPad

    Bimbo sluts, these two make me want to puke. They’re represent all that is wrong with the world and the values that most sick, sad people have.

  49. Pete Wentz is a moron.

  50. Irene

    She looks a lot like Britney Spears in these pictures!

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