cant wear briefs anymore

superslam

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good lord! i have a pair of green boxer briefs that i got just to see how the bulge looks in them (you can see on my xtube...name is clemson1232003). anyways after wearing them for a full night, my dick hurt so bad this morning when i woke up. i honestly thought it was silly to think that I was too big to fit comfortably in briefs anymore, but it was one of the more painful things ive ever put my cock through! so im not going to try that again, at least not normal sized underwear. the problem is that im quite slender, body wise, so i need small-medium underwear. i just dont fit in that tho!
 

superslam

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hah i think ill get a pair of regular briefs just for shock value. i was out of clean boxers so I was forced to endure the boxer briefs again, so before i put them on i stretched out the pouch with my hands, much nicer..
 

midlifebear

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Definitely stick with boxers and loose-fitting (in the crotch at least) jeans. Last time I was fitted for a suit the crotch was too high and after wearing it the first night it felt like I had a hernia the next day because I'd had to keep my member wrapped half-way around my waiste. Not to mention the chafing. So much for buying "off-the-rack." When you're older you'll appreciate developing a working relationship with a good tailor. Now that I'm "retired" I wear surfer-length shorts with the jockey-brief pockets cut out of them. Life's much better with my boys hanging loose and my unit free to swing.

Good luck with that.