Are these comfortable for a guy with a smaller penis

You can wear them as regular underwear. Using the sheath set up is completely optional. The fabric is super soft and comfortable and they are well made

Are they good for truck drivers? Sitting all day.

They solved my problem of driving and sitting on my sack. I was also worried about flying in cramped seating and not being able to position my stuff. Short of having someone hold them up while I drive, these are the best answer I have found. Get a pair and try them out.

How do i pick the size for this product?

If your waist size is between 32-38=large. However, there is a sizing chart on both Amazon and the Sheath website. I love this brand!

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Save 17% by adding 4.0 sheath to your cart 1 x 4.0 sheath underwear It is composed of 95% modal and 5% elaster. Equipped with a newly developed round dual sheath to separate the pole and gemstone. Designed in the style of traditional boxer briefs that are appreciated by professional athletes, health and fitness enthusiasts, bodybuilders, yoga practitioners, martial arts, and anyone looking for unmatched comfort while meeting the demands of life. Builders, yoga practitioners, martial arts, or anyone seeking unmatched comfort while meeting the demands of life.