Ok, maybe kinda funny. But serious! And maybe not frostbite, but frostnip. But "Penis Frostnip" sounded like a band. Anyways...

 

Last year was the first time I rode year long in Chicago, commuting straight through the winter, as many of you do. On more than one occasion I experienced some painfully cold moments on one specific appendage. Tonight, on this mid-September evening, with the bike chill in the lower 40's, it definitely brought back some of those more unpleasant winter bike riding memories.

 

Aside from a third sock, any pro-tips or suggestions for proper protection?

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Bike for Life, How to ride to 100, by Roy Wallack and Bill Katovsky doesn't mention frostbite per se (that I remember), but there is a whole chapter on protecting genitals.
Thermal underwear or bike specific thermal shorts...or a hand warmer strapped to your saddle
You can get briefs or shorts with windblocking material in the front.  E.g. the craft gunde shorts .  I've found that they work pretty well.  Alternatively, shove a sock with a handwarmer inside down your pants.
Im so glad I dont have this problem but I will say there is a corollary for women in the northern hemisphere.

Unrelated, but there is a absolute classic story about this in the running community:

http://books.google.com/books?id=wAa9qq9kbncC&pg=PA254&lpg=...

 

Local author Dave "Mr. Bike" Glowacz advises, "To avoid unusual frostbite wear a wind brief. Avoid porous sweatpants." on p. 214 of his great guide Urban Biker's Tips and Tricks.
ouch that Lore of Running paragraph hurts to read.
I made a shield out of a piece of faux shear-ling - works great.  I actually thought that I should market them under the name "Cock Block"
I handknit and crochet cock cozys! They cover the "whole package". Message me if your interested.

Try something like the Ibex Wind Brief:

http://shop.ibex.com/Apparel/Mens-Boxers/M-Zepher-Wind-Boxer

 

I wear merino briefs on cold days (actually all year). I can vouch for the ibex briefs.

Wear a cod piece. Maybe you will be ahead of the curve and hipsters will start wearing them. Then you could ligitimaly say that you did it before it was coor.

 

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