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This Guy Takes His Cock to Hell and Back

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There's nothing better than exploring a new kink, we just hope people do them smartly and safely—unlike this guy, who doesn't seem to hurt himself, but he's none too smart.

Here, Xtube's IBot69 made a little movie for us using a chastity and restraint device called the Five Gates of Hell, which is one ring that goes around the cock and balls a la cockring and four rings that slip over the shaft to keep you from touching your johnson. That's why it's hell. Well, this guy tries to jerk off with it. At least he admits that he thinks he did it wrong. And speaking of hell, his deep and somewhat distorted voice sounds fantastically demonic!

. . .

&MiddotDiscovering 5 Gates of Hell (xtube.com)

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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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