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Q: Does the head print go down or up when putting it on?

I think downward! I purchased this to see if it would provide extra modestly. To create a smoother appearance, even with pleated pants, so people would not stare. Yep, born with a lifetime of embarrassment! I got tired of trying this type, it smoothed things out, but added more bulk, which is not good. I’ve heard of people using a piece of bread to help smooth out their appearance, especially for male models, modeling small tight pieces of clothing. All to hide the “big fat obvious head”. Yes, not proud, mostly embarrassed!!!

Q: It looks like it should be longer if it’s size you want. But if it’s modesty you want looks like it would cover “it” up only to be shaped like ”it” ?

First, I notice that the image that accompanies this question has the version of the product with an "embossed" penis in slight relief on the front. There are versions - the kind I have - that are plain (smooth, no embossed penis in bas-relief). Regarding size; for an average guy's anatomy (you can google what average is) Everything fits within the cup when flacid, it is just right. When penis size is somewhere in between flaccid and erect it may rise above the cup. Seriously, that has not been a frequent problem but there are moments. I use my cup primarily in underwear that have a contour pouch, and yoga shorts because the lift keeps the package up and out of the way for certain poses., and it works great - comfortable and nice clean lines for modesty There is a little size enhancement that could be noticed if someone is looking but mostly it is just a better positon for the testicles while doing cross-legged poses like Garudasana (Eagle pose) , Ardha Matsyendrasana (half Lord of fishes) etc.