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Birthday Boy Toy: Matt Dillon’s Dumper

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Matt Dillon (52)

Don't worry if Matt Dillon hasn't been on your radar since You, Me, and Dupree (2006), because he hasn't really been on anyone's radar! Thanks to his cute little butt in Factotum (2005), however, he will not be forgotten. Also, are we seeing some balls between his thighs? 

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  • May 2, 2025
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    Hey Chad,

    I am typically a top and have limited experiences bottoming, and the reason is because it hurts too much. Every time I go through the same thing, clean out, hype myself up, poppers, lube, and try taking it slow. But the outcome is always the same, it hurts and I can’t enjoy myself and then stop him after a few minutes because it is too unbearable. How do I bottom without it feeling like I’m passing a watermelon?

    Thanks,

    - Novice Bottom
    Chad,

    There’s nothing that ticks me off more than a flake, and lately, I keep getting ghosted on the apps. I get tons of messages when I first log on but by the time I am ready, or the later it gets, the more likely they are to flake on me and then I end up finishing myself and going to sleep. How do I get a hookup to come through?

    SOS,

    - Night Owl
    Dear Chad,

    I am a little annoyed to have to even ask this but what is the policy on paying for dates? I recently went out with a guy for the second time now and I had to pay for everything BlOTH TIMES. He didn’t even reach for his wallet when the waiter brought the bill, or when we went to the movies! I feel like that’s so rude, like it should be his turn the second time right? Or do I have to say something about splitting the bill from the beginning? 

    Thanks,

    - NotUrSugarDaddy
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