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Bo On Top
Bo On Top
COCKSURE MEN

Bo Dean is a Cocksure Men exclusive. He’s about as straight as any straight man can be. Of course, when it comes to making money, some straight men will...

Barebacking Fuck Buddies
Barebacking Fuck Buddies
COCKSURE MEN

Cocksure Men has had a lot of success with their RAW series on the web. Barebacking is a popular genre that’s quickly gaining fans ‘ and they’re demanding to...

Taylor Made Adventures in Barebacking
Taylor Made Adventures in Barebacking
COCKSURE MEN

Fans of David Taylor will definitely want to add this compilation of his work at Cocksure Men to their DVD collection. This hunky mega porn star with giant arms and...

Return to Sun Valley Bareback
Return to Sun Valley Bareback
COCKSURE MEN

The boys of Sun Valley are back, bringing you more of their bareback adventures that only Cocksure Men can bring. Last time, they offered a great selection of their models...

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Cybersocket Ask Chad
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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