Ashlee Simpson’s in a Bikini

September 26th, 2011 // 107 Comments

Under the watchful, always watchful eyes of Papa Joe, the whole Simpson clan slipped down to Mexico for a little family vacay over the weekend where Ashlee brought her new boyfriend and pranced around in a bikini as Jessica hid under a poncho. Not so much out of shame, as much as she had pork pockets installed. Except surprisingly absent was little Bronx Mowgli who’s probably sitting at home right now watching Pete Wentz wonder when Ashlee’s going to get back from the store. “She said she’d just be a minute. But if I call, she’ll get mad. Oh, fiddlesticks!”

Photo: Splash News


  1. I think I would hit that.

    I might hate myself later on in life but I would do terrible things to her butthole.

  2. Ashlee Simpson Bikini
    Commented on this photo:

    She walks like Jessica Rabbit.

  3. Ashlee Simpson Bikini
    Commented on this photo:

    Nice ass for once, I am impressed. Never though she was the least bit hot. She isn’t thick like her sister but her legs still look nice. Hell with the boobs

  4. i’d hit it. while lipsyncing sweet nothings in her ear. then i’d “got get a sixpack” but really just skip back to the US

  5. Hello, Mexico? Hi. I am calling to recommend a couple of beheadings…what does your schedule look like, say, this afternoon?

  6. Ashlee Simpson Bikini
    Commented on this photo:

    she’s floating. she must be a demon…

  7. Ashlee Simpson Bikini
    Commented on this photo:

    Who is the bitch with the tits? Ashlee should get herself some of those.

  8. Ashlee Simpson Bikini
    Commented on this photo:

    Ashlee cums right thru her bikini bottoms when Dad talks about going back to their room for a little “Mean Daddy/Naughty Daughter” role play.

  9. Cock Dr

    Dat ass does not excuse her complete lack of talent.

  10. Alex

    Her boyfriend looks a lot like her dad.

  11. DogBoy

    she’s squirting in image #4

  12. Ashlee Simpson Bikini
    Commented on this photo:

    i notice in all these pics joe never stands up. too embarrassed to, hmm?

  13. Ashlee Simpson Bikini Jessica Simpson Blanket
    Cock Dr
    Commented on this photo:

    What a fashionable blanket Jess is hiding under.
    I completely understand though. A daily diet of beer, queso & guacamole really packs on the pounds.

  14. old man

    Appears papa joe has replaced the defective jessica model with a new buxom brunette. ashlee still orgasms on command though.

  15. Ashlee Simpson Bikini
    Commented on this photo:

    no comment on the fact it LOOKS like she is peeing?!?!

  16. Ego, the living planet

    Damn, and I already had breakfast..

  17. Truth, just-ice and the rough way

    She’s an idiot and id rough it, doesn’t say much about my self estimate, non.

  18. Ashlee Simpson Bikini
    Ego, the living planet
    Commented on this photo:

    Do her knees not bend?

  19. Dude of Dudes

    Not pictured: Jessica breaching offshore for one of those whale tourist boats.

  20. Ashlee Simpson Bikini
    Commented on this photo:

    To hell with Ashlee, Who is that big titted one next to her?

  21. Ashlee Simpson Bikini
    Commented on this photo:

    How do you go from pastor to pimp? Ask Joe.

  22. Ashlee Simpson Bikini Jessica Simpson Blanket
    Commented on this photo:

    “sniff”…why is daddy messing with Ashlee?? My boobies are much bigger than hers and I haven’t pushed a kid out through my naughty part.

  23. Ashlee Simpson Bikini
    Commented on this photo:

    You call those breasts? Let me show you some pictures of your sister. Now these are breasts

  24. De Gaulle

    Holy shit? I may actually fap to #4!
    Off to the men’s room..

  25. Guesty

    Ha…Ashlee is so amazingly cunty that it’s nearly bewildering. She knows that Jessica has fat girl psychological issues, and doesn’t feel that bikini-ing it up is enough – she preens in every single shot in front of her beloved lardass sister, who Ashlee has pretty clearly always hated, since when Jessica’s in a room, Ashlee is number one in synching and face-transplanting but number two in earnings, talent, parental love (at least in terms of incest…that’s love, right?), facial symmetry and ability to keep her shit together whilst coked out.

  26. SarahK

    She is trying too hard yet again. So weird that her pervy dad is there while Ash posture her hips for the paps. Weirdo christian family.

  27. Racer X


  28. Richard McBeef

    You could make one fine bitch if those Simpson girls worked like Mr. Potato Head.

  29. Rocky

    He went down on her


    Bronx Mowgli came out of that? Pete Wentz came inside of that? Damn.

  31. Ashlee Simpson Bikini
    Commented on this photo:

    Wow she’s walking like she has no idea she is being photgraphed

  32. Ashlee Simpson Bikini
    Commented on this photo:

    Turn the fuck around, ugly

  33. Ashlee Simpson Bikini
    Señor Pedro
    Commented on this photo:

    The universally known “hide a boner” pose.

  34. Ashlee Simpson Bikini
    Ay Dios mio
    Commented on this photo:

    “Whatcha’ doodling there Daddy?”

  35. Ashlee Simpson Bikini
    Commented on this photo:

    That is one sweet ass.

  36. LJ

    If you do Ashley, does Joe sit other side of the two way mirror watching?

  37. Ashlee Simpson Bikini
    Ay Dios mio
    Commented on this photo:

    Ashlee: *shimmy shimmy shimmy*
    Joe: “Very good! No I do mean it. Now onto lesson number three..”

  38. BigOkie

    Trying awfully hard to “pose” the ass… and doing a pretty nice job of it actually. I must say I appreciate the effort.

  39. dong slayer

    Holy crap, is that her mom with the dark hair?? Why does she look better than her daughters?

  40. Ashlee Simpson Bikini
    Commented on this photo:

    I thought she had a sexy way of walking, but apparently her bikini bottom is just on crooked.

  41. MehdiN

    She looks like a baby deer learning to walk for the first time

  42. Clarence Beeks

    She has a cute butt, That is my say something nice.

  43. Ashlee Simpson Bikini
    Commented on this photo:

    I’m almost positive that he just said, “Hey sugar tits, why don’t you come over here and sit on Daddy’s lap for a while?”

  44. Ashlee Simpson Bikini
    Commented on this photo:

    Sugar dady someone?

  45. Ashlee Simpson Bikini Jessica Simpson Blanket
    Do Freebird
    Commented on this photo:

    First there was The China Syndrome. Now comes the ever more terrifying sequel, The Delta Burke Syndrome.

  46. Ashlee Simpson Bikini
    Do Freebird
    Commented on this photo:

    Some people would believe that she pulled the back of her bikini bottom down as a show of modesty in front of her father. I believe she pulled her bikini front up to display her nether lips for the pleasure of her father.

  47. Michael

    I can’t tell if she’s thin or not. I will say she’s in good shape. She was a good singer at some point (until the dreaded SNL performance, but people can rebound!). But if this is her new line of work… :.-(

  48. Ashlee Simpson Bikini
    Do Freebird
    Commented on this photo:

    Thank God there’s no giant TMZ superimposed all over this picture. It allows us to enjoy the pure (fap-fap-fap) degrading (fap-fap) incestuous (fap-fap-fap) nature of this without any distraction. OhhhhhhhhSweetRelease

    anyone have tissues?

  49. Sayo

    Is that Samantha Ronson? (STRAIGHT) LADIES – GROW OUT YOUR HAIR.

  50. Dan

    I dunno… seems like she would be dangerous to be in any relationship with – even a superficial fuck buddy one. It seems like you would be dragged somewhere you wouldn’t want to go.

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