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Funniest Story Ever

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  • Funniest Story Ever

    Tucker tries buttsex; hilarity does not ensue
    by Tucker Max

    I spent the summer between my 2nd and 3rd year of college suckling on the
    parental teat in South Florida. It was the absolute prime of my "do anything
    to get laid" phase. I was recently freed from a 4-year long-distance
    relationship that began in high school and I wanted nothing more than to
    have sex with as many girls as possible.

    Most of the things I did that summer are not story-worthy; you can only tell
    the same, "I got drunk on Dom and fucked this hottie" story so many times
    before it gets annoying. That summer I experienced every random sex
    situation that a 20 year old can imagine: fucking on the beach, getting head
    from random girls in club bathrooms, sleeping with 3 different girls in a
    day, getting so drunk I passed out during sex, getting arrested for
    receiving fellatio in the pool at the Delano, blah, blah, blah.Jesus. What
    does it say about how fucked up my life is that I don't consider these
    stories to be extraordinary anymore?

    Anyway, while most of my stories may not be extraordinary for me, there is
    one very notable exception.

    I was seeing one girl, "Jaime," about twice a week. She was a fresh arrival
    to South Beach, having moved there 5 months ago from upstate New York as a
    19 year old with a modeling contract. We met through a mutual friend who
    befriended her while they were shooting a TV commercial. Five weeks and lots
    of sex later, she thought we were dating. I knew better, but she was way too
    hot to bother correcting her assumption.

    The ex-girlfriend of 4-years I previously spoke about was very sexually
    conservative. It was missionary in the dark and then straight to sleep, with
    maybe a blowjob on the weekends if she'd had a few glasses of wine with
    dinner (it was a high school relationship, I didn't know any better). After
    four years of this, I was ready to experience all the things I'd missed out
    on (when I wasn't cheating on her, of course).

    Buttsex, known in the biz as "anal," was one of these unknowns, and I
    decided that I wanted to try it. Jaime was the perfect partner: very hot and
    very sweet, and more importantly, very na´ve and very open to suggestion.

    She was reluctant at first, not understanding why we just couldn't keep
    having normal sex, so I had to employ my persuasive powers:

    Jaime "But.I've never done it."
    Tucker "I've never done it either; it can be our thing."

    Jaime "But.I don't know if I'll like it."
    Tucker "You won't have to worry about getting pregnant."

    Jaime "But.I like normal sex."
    Tucker "Everyone's doing anal. It's the new black."

    Jaime "But.I don't know.it seems weird."
    Tucker "It's the preferred method in Europe. Especially with the runway
    models. Don't you want to do runways in Europe?"

    After a few weeks of this, she finally consented. Though she agreed to let
    me put my penis in her small hole, she extracted a promise in return:

    "OK, we can try anal sex, but I want it to be special and romantic. You have
    to take me out to a nice place, like The Forge or Tantra, NOT one of your
    parent's restaurants, and it has to be a weekend night, NOT a Monday. And
    you have to keep taking me out on weekends. I'm tired of being your Monday
    night girl."

    I made reservations for the next Friday at Tantra. Aside from being insanely
    expensive, Tantra is famous for having grass floors. Really; they put in new
    sod every week. They also advertise their food as "aphrodisiac cuisine."
    Yes, at that point in my life, I thought these things worked.

    Thanks to my father's connections, I got us a corner booth in the grass
    room. She was quite impressed. I ordered like it was the Last Supper. No
    expense was spared. Two $110 bottles of merlot, veal rack, stone crabs, the
    Tantra Love platter--it was lavish and decadent. I was 21, stupid, and
    wanted to fuck Jaime in the butt; I wasn't about to let a $400 tab get in my

    By the time we left Tantra, this girl had doe eyes that made Bambi look like
    a heroin-chic CK model. She could not have been more in love with me. The
    entire drive back to my place she was rubbing my crotch, telling me how
    badly she wanted to me to fuck her, how hot I made her, etc, etc. We get
    back to my place and our clothes are off before we even get in the door. We
    collapse on the bed and start fucking. Normal vaginal sex at first, just
    like always.

    Now, what she did not know, and what I have not told you yet, was that I had
    a surprise waiting for her.

    [Aside: Before I tell you what the surprise was, let me make this clear: As
    I stand right now, 27 as of this writing, I am a bad person. At 21, I was
    possibly the worst person in existence. I had no regard for the feelings of
    others, I was narcissistic and self-absorbed to the point of psychotic
    delusion, and I saw other people only as a means to my happiness and not as
    humans worthy of respect and consideration. I have no excuse for what I did;
    it was wrong and I regret it. Even though I normally revel in my outlandish
    behavior, sometimes even I cross the line, and this is one of those
    situations..but of course, I'm still going to write about it.]

    This was going to be my first time foraging in the ass forest, and I wanted
    to have a reminder of my trip, a memento I could carry with me the rest of
    my life.so I decided to film us.

    I planned this beforehand, but I was afraid she would decline, so instead of
    being mature and discussing this with Jaime, I just made the executive
    decision to get it on camera.without telling her.

    That alone is pretty bad. But instead of just setting up a hidden camera.I
    got my friend to hide in my closet and film it.

    No really--I know that I will burn in hell. At this point, I'm just hoping
    that my life can serve as a warning to others.

    I left my door unlocked and we arranged it so that around midnight my friend
    would go over to my place and wait until my car pulled in, and then run into
    the closet and get the camera ready. The top half of the closet door was a
    French shutter, so it was easy to move the slats and give him a decent
    camera shot through the closed door.

    By the time Jaime and I got to the bed, I was so drunk I had forgotten that
    he was filming this, and of course she had no idea he was there. After a few
    minutes of standard sex, she kinda stopped and said, all serious and in her
    best seductive soap opera voice, "I'm ready."

    I quickly flipped her over and grabbed the brand new bottle of AstroGlide I
    had on my bedside table.

    A week prior, after Jaime consented to buttsex, I realized that I didn't
    have any idea how to do it. How exactly do you fuck a girl in the ass?
    Luckily, I had the world's best anal sex informational resource at my
    disposal: The gay waiter. I consulted several gay waiters who worked at one
    of my parents restaurants about the mechanics of buttsex, and each one
    recommended AstroGlide as the lubricant of choice. Much to my dismay, I
    learned that spitting on your dick is not enough lube for buttsex. Stupid,
    lying porn movies.

    The other important piece of advice I remembered was from Calvin, "Make sure
    you use enough, because if this is her first time, she'll be especially
    tight, and it might hurt her. Use enough to really loosen her up and go slow
    until she gets used to it. Then it's smooth sailing from there."

    Well, since some is good, more is better, right? At 21, this seemed logical.

    I opened the cap, crammed the bottle top into her asshole, and squeezed. I
    probably emptied half of the 4-ounces of AstroGlide into her. I have since
    learned from homosexuals that a 4-ounce bottle usually lasts them about 6
    months. So yeah--I overdid it.

    But Tucker Max wasn't done. Oh no, after depositing enough grease in her to
    run a Formula One racecar, I dumped half of what remained onto my cock and
    balls, really wanting to lube up because I didn't want her to be

    Really--consider my thought process: I was going to fuck her in the butt and
    film it without her consent, yet I was truly concerned about her personal
    comfort. Sometimes the contradictions in my personality even amuse me.

    Predictably, I slid in with ease. She was a little tense at first, but with
    an Exxon Valdez size load spilled into her poop chute, she quickly loosened
    up and got into it. I liked it also; it had a different feel to it. Not as
    good as vaginal sex, a little grainy, kinda tight, but still very nice.

    Before I knew it I was fucking her like the apocalypse was imminent, burying
    it to the hilt with impunity. After a few minutes I was ready to come. My
    urgency was expressed in my tempo, and I began really jackhammering her. As
    the excitement got the best of me, I pulled out too far and my dick came out
    of her ass. I kinda scrambled to grab my dick and put it back in so I could
    finish off inside of her, but before I could even get a hold of it and put
    it back in her ass, I heard a faint "psssst" sound and felt something wet
    and warm hit my crotch.

    It was dark in the room (I was not smart or sober enough to leave the lights
    on for the camera), so after I looked down it took me a few seconds to
    realize that my dick, balls and groin area were covered in a viscous black
    liquid. I stopped moving and stared at my strangely colored crotch for a
    good 5 seconds, completely confused, until I realized what happened:

    "Did you.did you just.shit on my dick?"

    I reached down to touch the liquid feces, still in complete and utter
    disbelief that this girl shot explosive diarrhea on my penis, when, without
    warning, the smell hit me.

    I have a very sensitive nose, and I have never been more repulsed by a smell
    in my life. The combination of synthetic AstroGlide and rancid stench of raw
    fecal matter combined to turn my stomach, which was full of seafood, veal
    and wine, completely over.

    I tried to hold it back. I really did everything I could to stop myself, but
    there are certain physical reactions that are beyond conscious control.
    Before I knew what I was doing, it just came out:


    I vomited all over her ass. Into her crack. Into her asshole. On her ass
    cheeks. On the small of her back. Everywhere.

    She turned her head, said, "Tucker, what are you doing?," saw me vomiting on
    her, screamed "Oh my God!," and immediately joined me:


    Watching her throw up on my bed made me vomit even more. Her vomiting all
    over my bed, me vomiting on her ass, the next step was almost inevitable.

    I heard the loud CRASH first, turned to see my friend break through the
    shutters and rip the closet door off as he, the video camera, and the door
    tumbled out of the closet and crashed onto the floor next to us:


    The memory of the 2-second span where all three of us were vomiting at once
    is permanently seared into my brain. I have never heard anything like that
    symphony of sickness. It was like something out of the old Pink Panther

    I think the crowning moment was when my eyes locked with Jaime's, I saw her
    moment of realization and then her quick shift from shock and surprise to
    complete and irreparable anger. Between bouts of hurling she flipped out:


    She tried to stand up, slipped on the huge puddle of backflow AstroGlide on
    the bed, and fell into both my pile and her pile of vomit, covering her body
    and hair in vomit, shit and anal lubricant. She flailed on the bed for a
    second, grabbed the top sheet, wrapped it around her, and started running
    out of my place. Still naked and retching, my dick covered in shit and oil,
    I followed her as far as my front door.

    The last contact I ever had with her is the image I witnessed of her in a
    dead sprint, a

    shit, vomit and grease stained sheet stuck to her body, running from my


    The camera we used was one of those old fragile ones that filmed onto a VHS
    tape, and when he crashed out of the closet, the tape recorder and tape
    broke. It didn't occur to us at that the tape records the images
    magnetically, and we could take the actual tape itself and get someone to
    put it in another holster until after we had thrown it out. I know it seems
    stupid now, and believe me I kick myself about it everyday, but you should
    have seen the apartment afterwards--the tape was not a high priority.
    AstroGlide, shit and vomit covered EVERYTHING.

    I had to rent one of those steam cleaners, buy a new mattress, and I STILL
    lost my deposit. It was impossible to get the smell out. The next month was
    like living in a sewer. Every girl I brought back to my place after that
    refused to stay there, and some even refused to sleep with me anywhere
    because of how my place smelled.

    What I never found out, and I still want to know, is how the girl got home.
    I never heard from her again, and the mutual friend who introduced us called
    her but didn't get her calls returned. I never heard anything about her or
    from her again, even though she left her clothes and ID at my place (she
    wore a tight dress out that night, and didn't bring a purse or any money
    with her).

    Can you picture that scene? What did she do, hop in taxi? Wave down a
    passing car? Get on the bus? She lived at least 30 miles away, there is no
    way she walked home. It perplexes me to this day.
    (somebulls Free Mmorpg maker (somebulls

  • #2
    that shit is gross!!!


    • #3
      i had fun readin that!llool.. hilarious.. disgusting but hialrious
      REP 4 ME=REP 4 U
      BUN B BITCHES!!!


      • #4
        im really doubting this happened to ya, but it was a funny ass story
        Super Bowl XLI Champions

        Indianapolis Colts

        XBox Live Tag:


        • #5
          posted a few weeks ago, douche.
          My other aliases:
          On The Shelf

          Originally posted by Nasen
          i seeth for a minute
          Originally posted by Derty JaSoN
          i have no clue who was de-re whatever


          • #6
            That was an interesting story. Really gross though.
            no dough ho, you can't fuck with me!


            • #7
              lol @ the thought of 3 people in one room all puking all over each other, up to the knees in AstroGlide and shit. Kinda disgusting.
              aka cryptorchild


              • #8
                that shit was great


                • #9
                  omfg that was hilarious! definitely the funniest (sex) story i┤ve ever heard!


                  • #10


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