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Drunken Leo Wakes Up In a Bareback Dungeon at Anal Discipline

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Drunken Leo Wakes Up In a Bareback Dungeon at Anal Discipline

Drunken Leo Wakes Up In a Bareback Dungeon at Anal Discipline

Drunken Leo Wakes Up In a Bareback Dungeon at Anal Discipline

Drunken Leo Wakes Up In a Bareback Dungeon at Anal Discipline

When you have one too many drinks at a gay disco on a Saturday night, you never know what may happen. In Leo's case, one minute he was knocking back his fifth Jeigermeister shot and the next thing he knew he was in Jorge's dungeon wearing a leather collar, with his gaping asshole in the air and Jorge fucking his ass bareback like a piledriver. Luckily, Leo relishes the chance to be a subordinate fuck slave and this hot update from Anal Discipline turns out to be a load-swapping match made in bareback heaven.

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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?

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- 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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